Potassium Carbonate → HCID 44223673, compound

HRID 2196674Notes

Reaction equation

HRID 2196674 reaction equation
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[C:44]([NH:45][S:46]([CH2:49][CH2:50][CH3:51])(=[O:48])=[O:47])=[CH:43][CH:42]=[C:41]([F:52])[C:9]=1[C:10]([NH:12][C:13]1[CH:14]=[C:15]2[CH:21]=[C:20]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([CH3:31])[CH:26]=[CH:25]4)[N:19](S(C3C=CC=CC=3)(=O)=O)[C:16]2=[N:17][CH:18]=1)=[O:11]>CO>[F:7][C:8]1[C:44]([NH:45][S:46]([CH2:49][CH2:50][CH3:51])(=[O:48])=[O:47])=[CH:43][CH:42]=[C:41]([F:52])[C:9]=1[C:10]([NH:12][C:13]1[CH:14]=[C:15]2[CH:21]=[C:20]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([CH3:31])[CH:26]=[CH:25]4)[NH:19][C:16]2=[N:17][CH:18]=1)=[O:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67156075HCID 67156075, compound

Product 1

HCID 44223673HCID 44223673, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

2N K2CO3 (1 mL) was added to a solution of 2,6-difluoro-N-(2-(1-methyl-1H-indol-5-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (19 mg, 29 mmol) in MeOH (3 mL), and the mixture was heated to 60° C. for 16 hours. The volatiles were removed under reduced pressure, and the resulting residue was partitioned between EtOAc and water. The layers were separated, and the organic layers were dried (MgSO4), filtered and concentrated. Dichloromethane was added to the residue, and the resulting solid was collected by vacuum filtration giving 2,6-difluoro-N-(2-(1-methyl-1H-indol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (10 mg, 66%). 1H NMR (400 MHz, DMSO-d6) δ 12.04 (s, 1H), 10.84 (s, 1H), 9.80 (s, 1H), 8.33-8.28 (m, 2H), 8.15 (s, 1H), 7.77-7.73 (m, 1H), 7.57-7.52 (m, 2H), 7.39-7.38 (m, 1H), 7.29-7.25 (m, 1H), 6.86 (s, 1H), 6.50-6.49 (m, 1H), 3.83 (s, 3H), 3.15-3.11 (m, 2H), 1.83-1.73 (m, 2H), 1.03-0.98 (m, 3H); m/z (APCI-neg) M−1=522.2.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe resulting residue was partitioned between EtOAc and water
  3. customThe layers were separated
  4. dry with materialthe organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionDichloromethane was added to the residue
  8. filtrationthe resulting solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-9ef8310c20994c05a0f384226878aca5
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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