Sodium Carbonate → HCID 58626079, compound

HRID 1161687Notes

Reaction equation

HRID 1161687 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](N2CCOCC2)[N:5]=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[CH:3]=1.[C:26]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)(=[O:28])[CH3:27].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][C:22]([F:23])([F:24])[F:25])=[CH:19][CH:20]=2)[N:5]=[C:6]([C:33]2[CH:34]=[C:29]([C:26](=[O:28])[CH3:27])[CH:30]=[CH:31][CH:32]=2)[N:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343103-Acetylphenylboronic acidHCID 58626081HCID 58626081, compound

Product 1

HCID 58626079HCID 58626079, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of compound (6-chloro-2-morpholin-4-yl-pyrimidin-4-yl)-(4-trifluoromethoxy-phenyl)-amine (0.5 g, 1.54 mmol) and 3-acetyl benzene boronic acid (0.125 g, 0.31 mmol) in DMF (10 mL) was added palladium tetrakis triphenyl phosphine (0.053 g, 0.046 mmol) and 2M Na2CO3 solution (1.3 g, 12.34 mmol) at temperature in the range of 20-40° C. The reaction mixture was heated for 12 hours under nitrogen atmosphere. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate (3×10 mL). Combined the organic layers were concentrated and the residue was purified by column chromatography using 15% ethylacetate in petroleum ether to afford the desired compound (0.125 g, 20%) as a white solid.

Workup

  1. temperatureThe reaction mixture was heated for 12 hours under nitrogen atmosphere
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. concentrationwere concentrated
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-53e653dc181b413e9c5a5f137688b85b
Source dataset
uspto-grants-2010_10
Patent number
US07820654B2

Reaction notes

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