Sodium Bicarbonate → 5,6-difluoro-N-(4-(3-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine

HRID 252649Notes

Reaction equation

HRID 252649 reaction equation
[F:1][C:2]1[C:32]([F:33])=[CH:31][C:5]2[NH:6][C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]4[C:22]([C:23]5[CH:28]=[CH:27][N:26]=[C:25](SC)[N:24]=5)=[CH:21][CH:20]=[CH:19][N:18]=4)=[CH:12][CH:11]=3)=[N:8][C:4]=2[CH:3]=1.O[O:35][S:36]([O-:38])=O.[K+].[C:40]([O-])(O)=O.[Na+]>CO>[F:1][C:2]1[C:32]([F:33])=[CH:31][C:5]2[NH:6][C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]4[C:22]([C:23]5[CH:28]=[CH:27][N:26]=[C:25]([S:36]([CH3:40])(=[O:38])=[O:35])[N:24]=5)=[CH:21][CH:20]=[CH:19][N:18]=4)=[CH:12][CH:11]=3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 668627235,6-difluoro-N-(4-(3-(2-(methylthio)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine

Product 1

HCID 668629535,6-difluoro-N-(4-(3-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 100 ml dry round bottom flask was charged with 5,6-difluoro-N-(4-(3-(2-(methylthio)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine (0.82 g, 1.76 mmol) and sonicated in methanol (17.62 ml, 0.10 M) for 20 minutes. To this was added oxone (3.25 g, 5.29 mmol) and mixture stirred at RT for 2 days. The reaction mixture was cooled to 0° C. and basified with aq. NaHCO3. The resulting solids were filtered, washed with water, and dried under high vacuum to provide 5,6-difluoro-N-(4-(3-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine as a light yellow solid. MS m/z=495.1 [M+H]+. Calc'd for C23H16F2N6O3S: 494.47.

Workup

  1. customA 100 ml dry round bottom flask
  2. filtrationThe resulting solids were filtered
  3. washwashed with water
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-ba341ebd2a6d4b9abf8bd3d972e64940
Source dataset
uspto-grants-2011_01
Patent number
US07868177B2

Reaction notes

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