1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N⁵-(phenylsulfonyl)-5-(2-propyn-1-ylamino)indole

Base Information

• Chemical Name: 1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N⁵-(phenylsulfonyl)-5-(2-propyn-1-ylamino)indole
• CAS No.: 112764-65-5
• Molecular Formula: C₃₂H₂₅BrN₂O₄S
• Molecular Weight: 613.532

Synonyms:1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N⁵-(phenylsulfonyl)-5-(2-propyn-1-ylamino)indole

Chemical Property of 1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N⁵-(phenylsulfonyl)-5-(2-propyn-1-ylamino)indole

Chemical Property:

Purity/Quality:

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Technology Process of 1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N⁵-(phenylsulfonyl)-5-(2-propyn-1-ylamino)indole

There total 12 articles about 1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N⁵-(phenylsulfonyl)-5-(2-propyn-1-ylamino)indole 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:

N5-(Phenylsulfonyl)-5-amino-1-benzoyl-7-(benzyloxy)-3-methylindole (112764-63-3) → 1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N5-(phenylsulfonyl)-5-(2-propyn-1-ylamino)indole (112764-65-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C

2: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h

With N-Bromosuccinimide; sulfuric acid; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja00222a043

Reference yield:

N-(2-hydroxy-4-nitrophenyl)benzamide (38880-89-6) → 1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N5-(phenylsulfonyl)-5-(2-propyn-1-ylamino)indole (112764-65-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / K₂CO₃ / n-Bu₄NI / acetone / 16 h / Heating

2: 90 percent / Na₂S₂O₄ / tetrahydrofuran; H₂O / 30 h / Heating

3: pyridine / tetrahydrofuran / 18 h / 22 °C

4: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C

5: CH₂Cl₂ / 10 h / 23 °C

6: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C

7: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C

8: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h

With pyridine; lead(IV) acetate; hydrogenchloride; N-Bromosuccinimide; sodium dithionite; sulfuric acid; sodium hydride; potassium carbonate; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/ja00222a043

Reference yield:

N-[4-[(Z)-Benzenesulfonylimino]-2-benzyloxy-cyclohexa-2,5-dien-(Z)-ylidene]-benzamide (112764-62-2) → 1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N5-(phenylsulfonyl)-5-(2-propyn-1-ylamino)indole (112764-65-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) 10percent aq. HCl / 1.) CH₂Cl₂, 0 - 23 deg C, 12 h 2.) THF, 23 deg C, 12 h

2: 97 percent / N-bromosuccinimide / H₂SO₄ / tetrahydrofuran / 1 h / -23 °C

3: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h

With hydrogenchloride; N-Bromosuccinimide; sodium hydride; sulfuric acid; In tetrahydrofuran;

DOI:10.1021/ja00212a067

upstream raw materials:

propargyl bromide

5-amino-1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N⁵-(phenylsulfonyl)indole

N-(2-hydroxy-4-nitrophenyl)benzamide

N-[4-[(Z)-Benzenesulfonylimino]-2-benzyloxy-cyclohexa-2,5-dien-(Z)-ylidene]-benzamide

Downstream raw materials:

6-benzoyl-5-(benzyloxy)-1,2-dihydro-8-methyl-1-methylidene-3-(phenylsulfonyl)-3H-pyrrolo<3,2-e>indole

CC-1065

(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

(R)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo<1,2-b:4,3-b'>dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

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