Pyridine → 2-{4-[4-(Acetylamino)-2-fluorophenoxy]-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl 4-methylbenzenesulfonate

HRID 2192172Notes

Reaction equation

HRID 2192172 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:31][C:32](=[O:34])[CH3:33])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15]([S:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[CH:16]=[C:17]([CH2:18][CH2:19][OH:20])[C:10]=12.N1C=CC=CC=1.[C:41]1([CH3:51])[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1>ClCCl.C(OCC)(=O)C>[CH3:51][C:41]1[CH:46]=[CH:45][C:44]([S:47]([O:20][CH2:19][CH2:18][C:17]2[C:10]3[C:11](=[N:12][CH:13]=[CH:14][C:9]=3[O:8][C:7]3[CH:6]=[CH:5][C:4]([NH:31][C:32](=[O:34])[CH3:33])=[CH:3][C:2]=3[F:1])[N:15]([S:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)(=[O:22])=[O:23])[CH:16]=2)(=[O:49])=[O:48])=[CH:43][CH:42]=1

Participants

6

Reactant 3

HCID 1049Pyridine2×HCID 73974-Toluenesulfonyl chloride2×HCID 59740986N-[3-Fluoro-4-({3-(2-hydroxyethyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]acetamide

Product 1

HCID 597409892-{4-[4-(Acetylamino)-2-fluorophenoxy]-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

50 mg (0.10 mmol) of N-[3-fluoro-4-({3-(2-hydroxyethyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo-[2,3-b]pyridin-4-yl}oxy)phenyl]acetamide are initially charged in 2.0 ml of dichloromethane. 25 μl (0.31 mmol) of pyridine and 19.7 mg (0.10 mmol) of p-toluenesulfonyl chloride are added, and the mixture is stirred at RT overnight. Two more times, the same amounts of pyridine and p-toluenesulfonyl chloride are added, at intervals of 2 hours. After the reaction has come to completion, the reaction solution is diluted with ethyl acetate and extracted twice with saturated ammonium chloride solution. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The crude product is purified by preparative HPLC.

Workup

  1. extractionextracted twice with saturated ammonium chloride solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customthe solvent is removed under reduced pressure
  4. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-d4a442f1150845c3a2a2124e3ac9354f
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

Loading…