3-[5-benzyloxy-2-(4-methoxybenzyloxy)phenyl]-7-bromo-2-oxo-2,3-dihydroindole-1,3-dicarboxylic acid 1-allyl ester 3-methyl ester

Base Information

Chemical Name:3-[5-benzyloxy-2-(4-methoxybenzyloxy)phenyl]-7-bromo-2-oxo-2,3-dihydroindole-1,3-dicarboxylic acid 1-allyl ester 3-methyl ester
CAS No.:658051-12-8
Molecular Formula:C₃₅H₃₀BrNO₈
Molecular Weight:672.529
Hs Code.:

Synonyms:3-[5-benzyloxy-2-(4-methoxybenzyloxy)phenyl]-7-bromo-2-oxo-2,3-dihydroindole-1,3-dicarboxylic acid 1-allyl ester 3-methyl ester

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Chemical Property of 3-[5-benzyloxy-2-(4-methoxybenzyloxy)phenyl]-7-bromo-2-oxo-2,3-dihydroindole-1,3-dicarboxylic acid 1-allyl ester 3-methyl ester

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Technology Process of 3-[5-benzyloxy-2-(4-methoxybenzyloxy)phenyl]-7-bromo-2-oxo-2,3-dihydroindole-1,3-dicarboxylic acid 1-allyl ester 3-methyl ester

There total 8 articles about 3-[5-benzyloxy-2-(4-methoxybenzyloxy)phenyl]-7-bromo-2-oxo-2,3-dihydroindole-1,3-dicarboxylic acid 1-allyl ester 3-methyl 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: 99.0%

: 2937-50-0
Allyl chloroformate

: 658051-11-7
3-[5-benzyloxy-2-(4-methoxybenzyloxy)phenyl]-7-bromooxindole-3-carboxylic acid methyl ester

: 658051-12-8
3-[5-benzyloxy-2-(4-methoxybenzyloxy)phenyl]-7-bromo-2-oxo-2,3-dihydroindole-1,3-dicarboxylic acid 1-allyl ester 3-methyl ester

Guidance literature:: With dmap; sodium hydride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 0.166667h;
DOI:10.1021/ol036179a

Reference yield:

: 20780-74-9
7-bromoisatin

: 658051-12-8
3-[5-benzyloxy-2-(4-methoxybenzyloxy)phenyl]-7-bromo-2-oxo-2,3-dihydroindole-1,3-dicarboxylic acid 1-allyl ester 3-methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran; hexane / 24 h / 20 °C

2.1: iPrMgCl / tetrahydrofuran / 0 - 20 °C

2.2: CH₂Cl₂ / 8 h / 40 °C

3.1: 11.2 g / K₂CO₃ / dimethylformamide / 12 h

4.1: iPr₂NEt; thionyl chloride / CH₂Cl₂ / 0.17 h / 0 °C

5.1: 1.2 g / AcOH; Zn / tetrahydrofuran / 7 h / 0 - 35 °C

6.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

6.2: 97 percent / tetrahydrofuran / 24 h / 33 °C

7.1: 100 percent / TAS-F / dimethylformamide / 1 h

8.1: 99 percent / NaH; DMAP / tetrahydrofuran; CH₂Cl₂ / 0.17 h / 20 °C

With dmap; thionyl chloride; isopropylmagnesium chloride; sodium hydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; tris(dimethylamino)sulfonium trimethylsilyldifluoride; zinc; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol036179a

Reference yield:

: 658051-07-1
7-bromo-1-(tert-butyldimethylsilanyloxymethyl)isatin

: 658051-12-8
3-[5-benzyloxy-2-(4-methoxybenzyloxy)phenyl]-7-bromo-2-oxo-2,3-dihydroindole-1,3-dicarboxylic acid 1-allyl ester 3-methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: iPrMgCl / tetrahydrofuran / 0 - 20 °C

1.2: CH₂Cl₂ / 8 h / 40 °C

2.1: 11.2 g / K₂CO₃ / dimethylformamide / 12 h

3.1: iPr₂NEt; thionyl chloride / CH₂Cl₂ / 0.17 h / 0 °C

4.1: 1.2 g / AcOH; Zn / tetrahydrofuran / 7 h / 0 - 35 °C

5.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

5.2: 97 percent / tetrahydrofuran / 24 h / 33 °C

6.1: 100 percent / TAS-F / dimethylformamide / 1 h

7.1: 99 percent / NaH; DMAP / tetrahydrofuran; CH₂Cl₂ / 0.17 h / 20 °C

With dmap; thionyl chloride; isopropylmagnesium chloride; sodium hydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; tris(dimethylamino)sulfonium trimethylsilyldifluoride; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol036179a