4-bromo-3-[2-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-indole-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:4-bromo-3-[2-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-indole-1-carboxylic acid tert-butyl ester
CAS No.:761433-65-2
Molecular Formula:C₃₃H₃₅BrN₂O₄Si
Molecular Weight:631.641
Hs Code.:

4-bromo-3-[2-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-indole-1-carboxylic acid <i>tert</i>-butyl ester

Synonyms:4-bromo-3-[2-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-indole-1-carboxylic acid tert-butyl ester

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Chemical Property of 4-bromo-3-[2-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-indole-1-carboxylic acid tert-butyl ester

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Technology Process of 4-bromo-3-[2-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-indole-1-carboxylic acid tert-butyl ester

There total 10 articles about 4-bromo-3-[2-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-indole-1-carboxylic acid tert-butyl 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:

: 52488-36-5
4-bromo-1H-indole

: 761433-65-2
4-bromo-3-[2-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-indole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / trifluoroacetic acid / 0.5 h / 25 °C

2: 87 percent / LiAlH₄ / tetrahydrofuran / 6 h / Heating

3: 79 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole hydrate / CH₂Cl₂ / 6 h / 25 °C

4: 82 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / tetrahydrofuran; H₂O / 4 h / 0 °C

5: 85 percent / o-iodoxybenzoic acid; DMSO / tetrahydrofuran / 4 h / 25 °C

6: 97 percent / TFAA; trifluoroacetic acid / CH₂Cl₂ / 8 h / 25 °C

7: 98 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 0.17 h / 0 °C

With dmap; lithium aluminium tetrahydride; dimethyl sulfoxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; 6: Robinson-Gabriel cyclodehydratation;
DOI:10.1021/ja040090y

Reference yield:

2-bromo-6-nitrotoluene: 55289-35-5
2-bromo-6-nitrotoluene

: 761433-65-2
4-bromo-3-[2-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-indole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: pyrrolidine / dimethylformamide / 5 h / 110 °C

1.2: 25.2 g / aq. HOAc; zinc / 3 h / 85 °C

2.1: 90 percent / trifluoroacetic acid / 0.5 h / 25 °C

3.1: 87 percent / LiAlH₄ / tetrahydrofuran / 6 h / Heating

4.1: 79 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole hydrate / CH₂Cl₂ / 6 h / 25 °C

5.1: 82 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / tetrahydrofuran; H₂O / 4 h / 0 °C

6.1: 85 percent / o-iodoxybenzoic acid; DMSO / tetrahydrofuran / 4 h / 25 °C

7.1: 97 percent / TFAA; trifluoroacetic acid / CH₂Cl₂ / 8 h / 25 °C

8.1: 98 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 0.17 h / 0 °C

With pyrrolidine; dmap; lithium aluminium tetrahydride; dimethyl sulfoxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 7.1: Robinson-Gabriel cyclodehydratation;
DOI:10.1021/ja040090y

Reference yield:

: 76271-74-4
2-((t-butyldiphenylsilyl)oxy)acetic acid

: 761433-65-2
4-bromo-3-[2-(tert-butyl-diphenyl-silanyloxymethyl)-oxazol-5-yl]-indole-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 79 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole hydrate / CH₂Cl₂ / 6 h / 25 °C

2: 82 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / tetrahydrofuran; H₂O / 4 h / 0 °C

3: 85 percent / o-iodoxybenzoic acid; DMSO / tetrahydrofuran / 4 h / 25 °C

4: 97 percent / TFAA; trifluoroacetic acid / CH₂Cl₂ / 8 h / 25 °C

5: 98 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 0.17 h / 0 °C

With dmap; dimethyl sulfoxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; 4: Robinson-Gabriel cyclodehydratation;
DOI:10.1021/ja040090y