{2-[7-(2-Methanesulfonyl-vinyl)-1H-indol-3-yl)-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester → {2-[7-(2-methanesulfonyl-ethyl)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester

HRID 1272229Notes

Reaction equation

HRID 1272229 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]([CH3:26])([CH3:25])[CH2:9][C:10]1[C:18]2[C:13](=[C:14]([CH:19]=[CH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]([CH3:26])([CH3:25])[CH2:9][C:10]1[C:18]2[C:13](=[C:14]([CH2:19][CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 86595247{2-[7-(2-Methanesulfonyl-vinyl)-1H-indol-3-yl)-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 69517243{2-[7-(2-methanesulfonyl-ethyl)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of {2-[7-(2-methanesulfonyl-vinyl)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (0.40 g, 1.02 mmol) in methanol (20.0 mL) is added 10% Pd/C (0.10 g) in methanol (2.0 mL). The reaction mixture is purged with hydrogen and hydrogenation is carried out with a hydrogen balloon overnight. The reaction mixture is filtered and the filtrate is evaporated to dryness to give 320 mg of {2-[7-(2-methanesulfonyl-ethyl)-1H-indol-3-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (80%). FDMS m/e=395.2 (M++1).

Workup

  1. customThe reaction mixture is purged with hydrogen and hydrogenation
  2. customis carried out with a hydrogen balloon overnight
  3. filtrationThe reaction mixture is filtered
  4. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-bd98aeb48a614cdeb7d5f49f62de46a2
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Reaction notes

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