Potassium Carbonate → HCID 11403394, compound

HRID 917715Notes

Reaction equation

HRID 917715 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([C:20]#[C:21][Si](C)(C)C)[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[C:6]([C:13]([NH2:15])=[O:14])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CO.C1COCC1>[C:20]([C:18]1[CH:17]=[CH:16][C:3]([NH:4][C:5]2[C:6]([C:13]([NH2:15])=[O:14])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=2)=[C:2]([F:1])[CH:19]=1)#[CH:21]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23630909HCID 23630909, compound

Product 1

HCID 11403394HCID 11403394, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

4-{2-Fluoro-4-[(trimethylsilyl)ethynyl]anilino}-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide was reacted with K2CO3 in MeOH/THF as for example 12, step B. The resulting crude product was purified by column chromatography on silica gel (50% acetone/CH2Cl2 as eluant) to give 4-(4-ethynyl-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a pale yellow-orange solid (73%), m.p. (CH2Cl2/MeOH) 269-272° C. 1H NMR [(CD3)2SO, 400 MHz] δ 10.60 (s, 1H), 8.37 (s, 1H), 7.91 (br s, 1H), 7.51 (t, J=8.4 Hz, 1H), 7.48 (br s, 1H), 7.46 (dd, J=11.4, 1.7 Hz, 1H), 7.33 (dd, J=8.3, 0.9 Hz, 1H), 5.71 (s, 1H), 4.25 (s, 1H), 3.37 (s, 3H). Anal. Calcd for C15H12FN3O2.0.25H2O: C, 62.2; H, 4.4; N, 14.5. Found: C, 62.6; H, 4.1; N, 14.6.

Workup

  1. customThe resulting crude product was purified by column chromatography on silica gel (50% acetone/CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-9e564b0d04884c83925ced79268a611a
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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