Water → 1H-Indole, 3-(5-bromo-2-chloro-4-pyrimidinyl)-1-[(4-methylphenyl)sulfonyl]-

HRID 1255991Notes

Reaction equation

HRID 1255991 reaction equation
[Br:1][C:2]1[C:3]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[H-].[Na+].[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.O>C1COCC1.CN(C=O)C>[Br:1][C:2]1[C:3]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([S:27]([C:24]3[CH:25]=[CH:26][C:21]([CH3:20])=[CH:22][CH:23]=3)(=[O:29])=[O:28])[CH:10]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 58071504HCID 58071504, compound2×

Product 1

HCID 580715031H-Indole, 3-(5-bromo-2-chloro-4-pyrimidinyl)-1-[(4-methylphenyl)sulfonyl]-Yield 73.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

3-(5-Bromo-2-chloropyrimidin-4-yl)-1H-indole (INTERMEDIATE 5, 1.23 g, 4 mmol) in THF (40.0 ml) and DMF (5 ml) was cooled to −10° C. Sodium hydride (0.19 g, 4.80 mmol) was added and the reaction was stirred at −10° C. for 30 min. 4-Methylbenzene-1-sulfonyl chloride (0.84 g, 4.40 mmol) was then added. The reaction mixture was allowed to warm to RT and stirred for 15 h. Water (10 mL) was added and the resultant solids were collected by vacuum filtration to give the title product (1.36 g, 73.5%).

Workup

  1. temperatureto warm to RT
  2. stirringstirred for 15 h
  3. filtrationthe resultant solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-1b23db05d40348428483f9f5124b87be
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

Loading…