Water → HCID 68717072, compound

HRID 1159828Notes

Reaction equation

HRID 1159828 reaction equation
[H-].[Na+].[F:3][C:4]([F:9])([F:8])[C:5]([OH:7])=[O:6].[CH3:10][N:11]([CH2:13][C:14]1[C:22]([OH:23])=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[CH:17][N:18]2[S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH3:12].I[CH2:34][CH3:35].O>CN(C=O)C>[F:3][C:4]([F:9])([F:8])[C:5]([OH:7])=[O:6].[CH2:34]([O:23][C:22]1[C:14]([CH2:13][N:11]([CH3:10])[CH3:12])=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:25])=[O:26])[CH:17]=[CH:16]2)[CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 68717753HCID 68717753, compound

Product 1

HCID 68717072HCID 68717072, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (95%) (101 mg, 4.23 mmol), was added to a solution of 4-[(dimethylamino)methyl]-1-(phenylsulfonyl)-1H-indol-5-ol (700 mg, 2.11 mmol; Example 131) in DMF (20 ml) at ambient temperature. The mixture was stirred for 15 min before iodoethane (0.203 ml, 2.54 mmol) was added. After 1 h water was added and the mixture extracted with Et2O. A small portion was purified on Gilson HPLC using 20-50% MeCN in 0.1% TFA. Yield: 65 mg; colorless oil. MS (ESI+) for C19H22N2O3S m/z 359 (M+H)+.

Workup

  1. additionwas added
  2. extractionthe mixture extracted with Et2O
  3. customA small portion was purified on Gilson HPLC

Sources & evidence

ORD record
ord-3bcb3b7221264e6eb575e088ac12adcc
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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