Dichloromethane → HCID 67549351, compound

HRID 2113459Notes

Reaction equation

HRID 2113459 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]#[N:5].[CH3:11][C:12]1[N:13]=[CH:14][NH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].ClCCl>CO>[F:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([N:15]2[CH:16]=[C:12]([CH3:11])[N:13]=[CH:14]2)[C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 746952,6-DifluorobenzonitrileHCID 178418800HCID 178418800, compound

Product 1

HCID 67549351HCID 67549351, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In analogy to example 5a, 2,6-difluoro-benzonitrile was reacted with 4-methylimidazole and potassium carbonate for 16 h at 90° C. After extractive workup and chromatography (SiO2, dichloromethane:methanol=100:0 to 98:2) the title compound was obtained as an off-white solid (yield: 29%). 1H-NMR (300 MHz, DMSO): δ=2.19 (d, J=0.8 Hz, 3H), 7.39 (s with fine splitting, 1H), 7.56-7.64 (m, 2H), 7.92 (mc, 1H), 8.04 (d, J=1.2 Hz, 1H).

Sources & evidence

ORD record
ord-cfd743ceda73450ca1db41c8896b4d60
Source dataset
uspto-grants-2008_10
Patent number
US07432256B2

Reaction notes

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