Allyl bromide → (S)-tert-butyl 2-(5-(N-allyl-N-(1,1,1-trifluoropropan-2-yl)sulfamoyl)pyridin-2-yl)-6-cyclopropyl-1H-indole-1-carboxylate

HRID 1028010Notes

Reaction equation

HRID 1028010 reaction equation
[CH:1]1([C:4]2[CH:12]=[C:11]3[C:7]([CH:8]=[C:9]([C:20]4[CH:25]=[CH:24][C:23]([S:26](=[O:35])(=[O:34])[NH:27][C@@H:28]([CH3:33])[C:29]([F:32])([F:31])[F:30])=[CH:22][N:21]=4)[N:10]3[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[CH2:42](Br)[CH:43]=[CH2:44]>CN(C=O)C>[CH2:44]([N:27]([C@@H:28]([CH3:33])[C:29]([F:31])([F:30])[F:32])[S:26]([C:23]1[CH:24]=[CH:25][C:20]([C:9]2[N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[C:11]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[C:4]([CH:1]2[CH2:3][CH2:2]2)[CH:12]=3)=[N:21][CH:22]=1)(=[O:35])=[O:34])[CH:43]=[CH2:42]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 66730765(S)-tert-butyl 6-cyclopropyl-2-(5-(N-(1,1,1-trifluoropropan-2-yl)sulfamoyl)pyridin-2-yl)-1H-indole-1-carboxylate

Product 1

HCID 66730659(S)-tert-butyl 2-(5-(N-allyl-N-(1,1,1-trifluoropropan-2-yl)sulfamoyl)pyridin-2-yl)-6-cyclopropyl-1H-indole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-tert-butyl 6-cyclopropyl-2-(5-(N-(1,1,1-trifluoropropan-2-yl)sulfamoyl)pyridin-2-yl)-1H-indole-1-carboxylate (503 mg, 0.99 mmol) and K2CO3 (276 mg, 2 mmol) in DMF (5 mL) was added allyl bromide (0.11 mL, 1.30 mmol). The mixture was stirred at room temperature for 2 hrs, and quenched with water (60 mL). The mixture was extracted with CH2Cl2 (3×20 mL). The solvent was then evaporated and (S)-tert-butyl 2-(5-(N-allyl-N-(1,1,1-trifluoropropan-2-yl)sulfamoyl)pyridin-2-yl)-6-cyclopropyl-1H-indole-1-carboxylate was obtained as a light yellow oil (500 mg, 92% yield). MS m/z 550.3 M+H+. This material was used in the next step without further purification.

Workup

  1. customquenched with water (60 mL)
  2. extractionThe mixture was extracted with CH2Cl2 (3×20 mL)
  3. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-377d69e8bcc440cd90ab95ff7db89921
Source dataset
uspto-grants-2014_05
Patent number
US08735414B2

Reaction notes

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