4-Chlorobenzaldehyde → HCID 44223172, compound

HRID 2196650Notes

Reaction equation

HRID 2196650 reaction equation
[OH-].[K+].[F:3][C:4]1[C:21]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:20][CH:19]=[C:18]([F:29])[C:5]=1[C:6]([NH:8][C:9]1[CH:10]=[C:11]2[CH:17]=[CH:16][NH:15][C:12]2=[N:13][CH:14]=1)=[O:7].[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=[O:36])=[CH:33][CH:32]=1>CO.CCOC(C)=O.[NH4+].[Cl-]>[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]([OH:36])[C:17]2[C:11]3[C:12](=[N:13][CH:14]=[C:9]([NH:8][C:6](=[O:7])[C:5]4[C:18]([F:29])=[CH:19][CH:20]=[C:21]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])[C:4]=4[F:3])[CH:10]=3)[NH:15][CH:16]=2)=[CH:33][CH:32]=1

Participants

7

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 14797Potassium HydroxideHCID 441994082,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide

Product 1

HCID 44223172HCID 44223172, compoundYield 58.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

KOH (0.012 g, 0.22 mmol) was added to 2,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (0.37 mL, 0.074 mmol) in MeOH (0.4 mL), followed by the addition of 4-chlorobenzaldehyde (0.013 g, 0.096 mmol). The reaction mixture was stirred at room temperature overnight. The contents were then diluted with EtOAc and NH4Cl (aq.) and extracted with EtOAc (3×). The organic layers were dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified via column chromatography (5% MeOH/DCM) to afford N-(3-((4-chlorophenyl)(hydroxy)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (23 mg, 58%). 1H NMR (400 MHz, CD3OD) δ 8.41-8.42 (m, 1H), 8.28-8.29 (m, 1H), 7.60-7.67 (m, 1H), 7.46-7.49 (m, 2H), 7.34-7.36 (m, 2H), 7.09-7.14 (m, 1H), 6.06 (s, 1H), 3.09-3.13 (m, 2H), 1.82-1.91 (m, 2H), 1.03-1.07 (m, 3H); m/z (APCI-pos) M+1=535.1.

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe organic layers were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified via column chromatography (5% MeOH/DCM)

Sources & evidence

ORD record
ord-4420afe618574094a0464ad507cca3e2
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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