Water → N-[2,4-difluoro-3-(5-pyridin-3-yl 1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-phenyl]-ethanesulfonamide

HRID 1964863Notes

Reaction equation

HRID 1964863 reaction equation
[NH2:1][C:2]1[C:3]([F:36])=[C:4]([C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH:18]=3)[N:13]([Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])[CH:12]=2)=[O:10])[C:5]([F:8])=[CH:6][CH:7]=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39].[CH2:42](N(CC)CC)C.O>C(Cl)Cl>[F:36][C:3]1[C:4]([C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH:18]=3)[N:13]([Si:26]([CH:30]([CH3:32])[CH3:31])([CH:33]([CH3:35])[CH3:34])[CH:27]([CH3:28])[CH3:29])[CH:12]=2)=[O:10])=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[NH:1][S:38]([CH2:37][CH3:42])(=[O:40])=[O:39]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59506753(3-amino-2,6-difluoro-phenyl)-(5-pyridin-3-yl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

Product 1

HCID 59506897N-[2,4-difluoro-3-(5-pyridin-3-yl 1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-phenyl]-ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (3-amino-2,6-difluoro-phenyl)-(5-pyridin-3-yl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (57, 35.0 mg. 0.069 mmol) in methylene chloride (6 mL) was added methanesulfonyl chloride (0.30 mL, 3.9 mmol) and triethylamine (0.40 mL, 2.9 mmol). The reaction was stirred at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated to give the crude compound that was used in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-308072f797724d41abb831b8e9673b19
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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