Potassium Carbonate → HCID 71558988, compound

HRID 578872Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:12]2([CH2:15]I)[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[F:17][C:18]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:19]=1[C:20]([NH:22][O:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[C:3]([C:12]2([CH2:15][N:22]([O:23][CH3:24])[C:20](=[O:21])[C:19]3[C:25]([F:29])=[CH:26][CH:27]=[CH:28][C:18]=3[F:17])[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

169 mg of 3-chloro-2-[1-(iodomethyl)cyclopropyl]-5-(trifluoromethyl)pyridine (step 3) and 110 mg of 2,6-difluoro-N-methoxy-benzamide were dissolved in dry dimethylsulfoxide under argon and 90 mg of potassium carbonate was added. The mixture was heated at 70° C. for 1 hour. Then ice water was added and the mixture was extracted with ether. The concentrated organic phase was purified on 30 g of silica gel, eluent hexane/ethyl acetate (4:1). Thus, 30 mg of N-[[1-[3-chloro-5-(trifluoromethyl)-2-pyridyl]cyclopropyl]methyl]-2,6-difluoro-N-methoxy-benzamide was obtained as a colorless resin. 1H-NMR (CDCl3): 8.70 ppm (s, 1H), 7.90 ppm (s, 1H), 7.32 ppm (m, 1H), 6.87 ppm (m, 2H), 4.24 ppm (s, 2H), 3.40 ppm (s, 3H), 1.19 ppm (m, 4H).

Workup

extractionthe mixture was extracted with ether
customThe concentrated organic phase was purified on 30 g of silica gel, eluent hexane/ethyl acetate (4:1)

Sources & evidence

ORD record: ord-f09c99c318b044abb1b55238e19a10d3
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040708B2

Reaction notes

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