2-(methylthio)ethyl 6-bromo-α-<(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl>-2,3-dihydro-2-oxo-1H-indole-3-acetate

Base Information

• Chemical Name: 2-(methylthio)ethyl 6-bromo-α-<(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl>-2,3-dihydro-2-oxo-1H-indole-3-acetate
• CAS No.: 94779-72-3
• Molecular Formula: C₂₃H₁₉BrN₂O₆S
• Molecular Weight: 531.384

Synonyms:2-(methylthio)ethyl 6-bromo-α-<(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl>-2,3-dihydro-2-oxo-1H-indole-3-acetate

Chemical Property of 2-(methylthio)ethyl 6-bromo-α-<(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl>-2,3-dihydro-2-oxo-1H-indole-3-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 2-(methylthio)ethyl 6-bromo-α-<(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl>-2,3-dihydro-2-oxo-1H-indole-3-acetate

There total 1 articles about 2-(methylthio)ethyl 6-bromo-α-<(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl>-2,3-dihydro-2-oxo-1H-indole-3-acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

2-[6-Bromo-2-oxo-1,2-dihydro-indol-(3E)-ylidene]-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-butyric acid 2-methylsulfanyl-ethyl ester (94779-71-2) → 2,3-dihydrophthalazine-1,4-dione (1445-69-8) + 2-(methylthio)ethyl 6-bromo-α-<(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl>-2,3-dihydro-2-oxo-1H-indole-3-acetate (94779-72-3)

Guidance literature:

With sodium dithionite; In ethanol; for 10h; Heating;

DOI:10.1016/S0040-4039(01)81451-9

Reference yield:

2-(methylthio)ethyl 6-bromo-α-<(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl>-2,3-dihydro-2-oxo-1H-indole-3-acetate (94779-72-3) → 1,5'-diacetyl-9'-(acetyloxy)-6-bromo-1,2,5',6',9',10'-hexahydro-9'-methyl-2,10'-dioxo-1',3'-bis(phenylmethoxy)spiro<3H-indole-3,8'-<8H>pyrido<1,2-f>pteridine>-7'-carboxylic acid (94779-85-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 27 percent / NH₂NH₂*H₂O / CH₂Cl₂; methanol / 0.5 h

2: 90 percent / NaHCO₃ / dimethylformamide / 1 h / Ambient temperature

3: 94 percent / Zn, AcOH / tetrahydrofuran / 10 h / 0 °C

4: 50 percent / pyridine / 2 h / 70 °C

5: 14 percent / NaBH₃CN, 2N aq. HCl / ethyl acetate / 0.17 h

6: 92 percent / benzene / 5 h / Ambient temperature

7: 83 percent / pyridine / Ambient temperature

8: 77 percent / Ac₂O / 2 h / 120 °C

9: 96 percent / 80percent m-CPBA / CH₂Cl₂ / 0.5 h / 0 - 25 °C

10: 82 percent / 0.1 M aq. NaHCO₃-Na₂CO₃ / acetone / 1 h / Ambient temperature; pH 10.2

With pyridine; hydrogenchloride; acetic anhydride; sodium cyanoborohydride; sodium hydrogencarbonate; sodium carbonate; hydrazine hydrate; acetic acid; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4020(01)86989-1

Reference yield:

2-(methylthio)ethyl 6-bromo-α-<(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)acetyl>-2,3-dihydro-2-oxo-1H-indole-3-acetate (94779-72-3) → C50H52BrN5O13 (90044-45-4,94841-56-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 27 percent / NH₂NH₂*H₂O / CH₂Cl₂; methanol / 0.5 h

2: 90 percent / NaHCO₃ / dimethylformamide / 1 h / Ambient temperature

3: 94 percent / Zn, AcOH / tetrahydrofuran / 10 h / 0 °C

4: 50 percent / pyridine / 2 h / 70 °C

5: 14 percent / NaBH₃CN, 2N aq. HCl / ethyl acetate / 0.17 h

6: 92 percent / benzene / 5 h / Ambient temperature

7: 83 percent / pyridine / Ambient temperature

8: 77 percent / Ac₂O / 2 h / 120 °C

9: 96 percent / 80percent m-CPBA / CH₂Cl₂ / 0.5 h / 0 - 25 °C

10: 82 percent / 0.1 M aq. NaHCO₃-Na₂CO₃ / acetone / 1 h / Ambient temperature; pH 10.2

11: 28 percent / picryl chloride / pyridine / 1.5 h / Ambient temperature

12: 72 percent / 0.1 N KOH / methanol / 2 h / Ambient temperature

13: 1.) Pb(OAc)4, 2.) NaBH₃CN / 1.) AcOH, room temp., 15 min, 2.) AcOH, room temp., 20 min

With pyridine; lead(IV) acetate; hydrogenchloride; potassium hydroxide; 2,4,6-trinitrochlorobenzene; acetic anhydride; sodium cyanoborohydride; sodium hydrogencarbonate; sodium carbonate; hydrazine hydrate; acetic acid; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4020(01)86989-1

upstream raw materials:

2-[6-Bromo-2-oxo-1,2-dihydro-indol-(3E)-ylidene]-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-butyric acid 2-methylsulfanyl-ethyl ester

Downstream raw materials:

C₂₅H₂₄BrN₅O₁₂

(8-Acetyl-2,4-bis-benzyloxy-7,8-dihydro-pteridin-6-yl)-[1-acetyl-6-bromo-2-oxo-1,2-dihydro-indol-(3E)-ylidene]-acetic acid 2-methylsulfanyl-ethyl ester

2-(methylthio)ethyl 8-acetyl-α-(1-acetyl-6-bromo-1,2-dihydro-2-oxo-3H-indol-3-ylidene)-5,6,7,8-tetrahydro-2,4-bis(phenylmethoxy)-6-pteridineacetate

2-(methylthio)ethyl 1,5'-diacetyl-6-bromo-1,2,5',6',9',10'-hexahydro-9'-hydroxy-9'-methyl-2,10'-dioxo-1',3'-bis(phenylmethoxy)spiro<3H-indole-3,8'-<8H>pyrido<1,2-f>pteridine>-7'-carboxylate

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