Potassium Carbonate → HCID 86618782, compound

HRID 1157569Notes

Reaction equation

HRID 1157569 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=[CH:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][N:3]=1.[N+]([O-])([O-])=O.[NH2:27][N+:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1.C([O-])([O-])=O.[K+].[K+].[Li+].[Cl-]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:10]3[CH:11]=[C:12]([NH:16][C:17](=[O:22])[C:18]([F:19])([F:20])[F:21])[CH:13]=[CH:14][CH:15]=3)=[N:27][N:28]3[CH:29]=[C:30]([F:34])[CH:31]=[CH:32][C:33]=23)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 68644196HCID 68644196, compoundHCID 86631082N-[3-(2-Chloro-pyrimidin-4-ylethenyl)-phenyl]-2,2,2-trifluoro-acetamide

Product 1

HCID 86618782HCID 86618782, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-[3-(2-chloro-pyrimidin-4-ylethenyl)-phenyl]-2,2,2-trifluoro-acetamide (See Example 1, step B) (5.0 g) in DMF (40 mL) were added 1-amino-3-fluoropyridinium nitrate (5.4 g) and K2CO3 (6.0 g). The reaction was kept stirring at RT for 1.5 h. The DMF solution was poured into 5% LiCl solution (60 mL) and extracted with EtOAc (2×30 mL). The combined organic phase were dried (Na2SO4) and concentrated. The crude products were separated through silica gel column chromatography to afford two products. The first to elute was N-{3-[3-(2-chloro-4-pyrimidinyl)-6-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide (2.0 g, 30% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.08 (d, 1H, J=5.49 Hz), 7.45 (d, 1H, J=7.68 Hz), 7.55 (t, 1H, J=7.96 Hz), 7.73-7.79 (m, 1H), 7.83 (d, 1H, J=0.91 Hz), 7.95 (t, 1H, J=1.74 Hz), 8.41 (dd, 1H, J=9.97, 5.76 Hz), 8.49 (d, 1H, J=5.49 Hz), 9.27 (dd, 1H, J=4.30, 2.29 Hz). ES-LC/MS m/z=436 [M+H]+.

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. dry with materialThe combined organic phase were dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude products were separated through silica gel column chromatography
  5. customto afford two products
  6. washThe first to elute

Sources & evidence

ORD record
ord-edf44eb9edda47d2bfec6c05a57066e1
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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