4-(1-Benzyl-3-carbamoylmethyl-2,7-dimethyl-1H-indol-5-yloxy)-butyric acid ethyl ester

Base Information

Chemical Name:4-(1-Benzyl-3-carbamoylmethyl-2,7-dimethyl-1H-indol-5-yloxy)-butyric acid ethyl ester
CAS No.:185501-70-6
Molecular Formula:C₂₅H₃₀N₂O₄
Molecular Weight:422.524
Hs Code.:

Synonyms:4-(1-Benzyl-3-carbamoylmethyl-2,7-dimethyl-1H-indol-5-yloxy)-butyric acid ethyl ester

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Chemical Property of 4-(1-Benzyl-3-carbamoylmethyl-2,7-dimethyl-1H-indol-5-yloxy)-butyric acid ethyl ester

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Technology Process of 4-(1-Benzyl-3-carbamoylmethyl-2,7-dimethyl-1H-indol-5-yloxy)-butyric acid ethyl ester

There total 12 articles about 4-(1-Benzyl-3-carbamoylmethyl-2,7-dimethyl-1H-indol-5-yloxy)-butyric acid ethyl ester 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: 63.0%

: 185501-69-3
4-[1-Benzyl-3-(carbamoyl-hydroxy-methyl)-2,7-dimethyl-1H-indol-5-yloxy]-butyric acid ethyl ester

: 185501-70-6
4-(1-Benzyl-3-carbamoylmethyl-2,7-dimethyl-1H-indol-5-yloxy)-butyric acid ethyl ester

Guidance literature:: With triethylsilane; trifluoroacetic acid; for 2h;
DOI:10.1021/jm960486n

Reference yield:

: 1076-74-0
5-methoxy-2-methyl-1H-indole

: 185501-70-6
4-(1-Benzyl-3-carbamoylmethyl-2,7-dimethyl-1H-indol-5-yloxy)-butyric acid ethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) NaCNBH₃, AcOH, 2.) 2N aq. NaOH / 1.) 4 h

2: tetrahydrofuran / 22 h / Heating

3: 1.) sec-butyllithium, N,N,N',N'-tetramethylenediamine / 1.) Et₂O, cyclohexane, -78 deg C, 1 h, 2.) Et₂O, cyclohexane, 16 h

4: 30 percent / trifluoroacetic acid / 17 h

5: 90 percent / NaH / dimethylformamide / 1 h

6: 80 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 0.25 h / 90 °C

7: 74 percent / BBr₃ / CH₂Cl₂ / 1 h

8: 72 percent / NaH / dimethylformamide / 16 h

9: CH₂Cl₂ / 0.75 h

10: NH₃ gas / CH₂Cl₂ / 0.5 h

11: NaBH₄ / ethanol / 24 h

12: 63 percent / triethylsilane, trifluoroacetic acid / 2 h

With triethylsilane; sodium hydroxide; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; ammonia; sec.-butyllithium; boron tribromide; sodium hydride; sodium cyanoborohydride; acetic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm960486n

Reference yield:

: 41568-27-8
(±)-5-methoxy-2-methylindoline

: 185501-70-6
4-(1-Benzyl-3-carbamoylmethyl-2,7-dimethyl-1H-indol-5-yloxy)-butyric acid ethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: tetrahydrofuran / 22 h / Heating

2: 1.) sec-butyllithium, N,N,N',N'-tetramethylenediamine / 1.) Et₂O, cyclohexane, -78 deg C, 1 h, 2.) Et₂O, cyclohexane, 16 h

3: 30 percent / trifluoroacetic acid / 17 h

4: 90 percent / NaH / dimethylformamide / 1 h

5: 80 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 0.25 h / 90 °C

6: 74 percent / BBr₃ / CH₂Cl₂ / 1 h

7: 72 percent / NaH / dimethylformamide / 16 h

8: CH₂Cl₂ / 0.75 h

9: NH₃ gas / CH₂Cl₂ / 0.5 h

10: NaBH₄ / ethanol / 24 h

11: 63 percent / triethylsilane, trifluoroacetic acid / 2 h

With triethylsilane; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; ammonia; sec.-butyllithium; boron tribromide; sodium hydride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm960486n