Sodium Carbonate → HCID 131735889, compound

HRID 2207358Notes

Reaction equation

HRID 2207358 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[N:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=2)[CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.Br[C:29]1[CH:30]=[CH:31][C:32]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[N:33][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.[Pd](Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([C:29]2[CH:30]=[CH:31][C:32]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[N:33][CH:34]=2)[CH:5]=[C:4]([NH:17][C:18]2[N:23]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:21]=[CH:20][N:19]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 53419964HCID 53419964, compoundHCID 58456089N-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine

Product 1

HCID 131735889HCID 131735889, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine (110 mg, 0.290 mmol), tert-butyl 2-(5-bromopyridin-2-yl)acetate (51.3 mg, 0.189 mmol), palladium(II) chloride (dppf) (28 mg, 0.038 mmol) and sodium carbonate (0.2 ml, 0.400 mmol, 2 M) in DMF (2 ml) was evacuated and purged with argon (3×), and then was irradiated in a microwave reactor for 10 minutes at 100° C. The mixture was filtered and purified on reversed phase HPLC to afford tert-butyl 2-(5-(3-methyl-5-((4-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)pyridin-2-yl)acetate (49.5 mg, 0.089 mmol). MS ESI calc'd. for C23H23F3N4O2 [M+H]+ 445. found 445.

Workup

  1. customwas evacuated
  2. custompurged with argon (3×)
  3. customwas irradiated in a microwave reactor for 10 minutes at 100° C
  4. filtrationThe mixture was filtered
  5. custompurified on reversed phase HPLC

Sources & evidence

ORD record
ord-d07f0df3b683463e875dcf575f1397ff
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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