Sodium Carbonate → HCID 86633492, compound

HRID 1255188Notes

Reaction equation

HRID 1255188 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:42]=[CH:41][C:12]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:26]=[C:25]([N:27]4[C:31]([C:32]([F:35])([F:34])[F:33])=[C:30]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:29]=[N:28]4)[CH:24]=[CH:23][CH:22]=3)=[CH:11][CH:10]=2)O1.Br[C:45]1[CH:46]=[N:47][C:48]([C:51]([F:54])([F:53])[F:52])=[CH:49][CH:50]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[F:34][C:32]([F:33])([F:35])[C:31]1[N:27]([C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][CH2:13][C:12]3[CH:11]=[CH:10][C:9]([C:45]4[CH:46]=[N:47][C:48]([C:51]([F:54])([F:53])[F:52])=[CH:49][CH:50]=4)=[CH:42][CH:41]=3)[N:26]=2)[N:28]=[CH:29][C:30]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27611975-Bromo-2-(trifluoromethyl)pyridineHCID 67159133HCID 67159133, compound

Product 1

HCID 86633492HCID 86633492, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a vial containing the title compound from Example 14 Step A (14.0 mg, 0.024 mmol) were added 3-bromo-6-trifluoromethylpyridine (6.4 mg, 0.028 mmol) and trans-dichlorobis(triphenylphosphine) palladium (II) (1.7 mg, 0.0024 mmol). Acetonitrile (0.500 mL) and sodium carbonate (0.059 mL, 1.0 M in water, 0.059 mmol) were added, and the resulting mixture was degassed by a nitrogen sparge. The reaction vial was capped and placed in a pre-heated oil bath (70° C.). After 6 h, the reaction mixture was allowed to cool to room temperature, then was purified by flash chromatography on silica gel: LCMS m/z 613.2 [M+H]+.

Workup

  1. customthe resulting mixture was degassed by a nitrogen
  2. customsparge
  3. customThe reaction vial was capped
  4. customplaced in a pre-heated oil bath
  5. custom(70° C.)
  6. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-8edff54c26aa4bcfa84e4e366e381861
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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