Potassium Carbonate → HCID 22732528, compound

HRID 1765261Notes

Reaction equation

HRID 1765261 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1.[NH:18]1[C:26]2[C:21](=[CH:22][C:23]([NH2:27])=[CH:24][CH:25]=2)[CH:20]=[CH:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[NH:18]1[C:26]2[C:21](=[CH:22][C:23]([NH:27][C:2]3[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]4[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=4)[N:3]=3)=[CH:24][CH:25]=2)[CH:20]=[CH:19]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 788675-AminoindoleHCID 14859904-Chloro-2-(pyridin-3-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 22732528HCID 22732528, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chloro-2-(3-pyridinyl)-6-trifluoromethyl-pyrimidine (42 mg, 0.162 mmol), 1H-5-indolylamine (31 mg, 235 mmol) and potassium carbonate (25 mg, 0.180 mmol) was heated overnight in 1 mL of DMF at 100° C. in a sealed tube. The reaction mixture was cooled to room temperature, diluted with 20 mL of ethyl acetate, washed with water (20 mL×3) and saturated NaCl. The organic layer was dried over Na2SO4, filtered, concentrated and the residue was purified by flash column chromatography (30% ethyl acetate/hexanes) to obtain the title compound as a white solid (mp 142–143° C., 45 mg, 0.127 mmol, 78%). 1H NMR (CDCl3): 9.56 (d, J=1.5 Hz, 1H), 8.74 (dt, J=1.8, 8.1 Hz, 1H), 8.63 (dd, J=3, 5.1 Hz, 1H), 7.66 (m, 1H), 7.46 (m, 2H), 7.30 (d, J=3 Hz, 1H), 7.19 (m, 1H), 6.82 (s, 1H), 6.55 (d, J=3 Hz, 1H).

Workup

  1. washwashed with water (20 mL×3) and saturated NaCl
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by flash column chromatography (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4427c384d1bc42cbbf4af5b6ae838bea
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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