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Potassium Carbonate → HCID 86618782, compound

HRID 1159966
Notes
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Reaction equation

HRID 1159966 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[C: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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 59511407HCID 59511407, compoundHCID 686441961-Amino-3-fluoropyridinium nitrate

Product 1

HCID 86618782HCID 86618782, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

To a solution of N-[3-(2-chloro-pyrimidin-4-ylethynyl)-phenyl]-2,2,2-trifluoro-acetamide (5.0 g) in DMF (40 mL) were added 1-amino-3-fluoropyridinium nitrate (5.4 g) and potassium carbonate (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+H)+=436.

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-f5e3d2b9c5ba4788ba03c5143f4b6063
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07812022B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes