Dimethylformamide → HCID 67335137, compound

HRID 2102228Notes

Reaction equation

Br[C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[CH:8]=[N:9][N:10]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[C:11]=2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[CH3:31][N:32](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:12]1([C:11]2[N:10]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:27])([F:26])[F:28])=[CH:20][CH:19]=3)[N:9]=[CH:8][C:7]=2[CH2:6][C:5]2[CH:4]=[CH:3][C:2]([C:31]#[N:32])=[CH:30][CH:29]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 782 mg 4-(4-bromobenzyl)-5-cyclohexyl-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazole from Step D above, 115 mg zinc cyanide, and 94 mg tetrakis(triphenylphosphine)palladium(0) in 5 mL DMF was heated under nitrogen in a 75° C. oil bath over night. Evaporate most of DMF. The residue was purified on silica gel using 10-40% EtOAc in hexanes to give the title compound as a yellowish solid. 1H NMR (CDCl3, 500 MHz) δ 7.61˜7.64 (m, 2H), 7.40˜7.44 (m, 2H), 7.33˜7.37 (m, 4), 7.31 (s, 1H), 4.06 (s, 2H), 2.70 (tt, J=3.1 & 12.5 Hz, 1H), 1.73˜1.79 (m, 4H), 1.66˜1.71 (m, 1H), 1.50˜1.58 (m, 2H), 1.09˜1.24 (m, 3H). LC-MS: 2.46 min. (M+H=426.2).

Workup

customEvaporate most of DMF
customThe residue was purified on silica gel using 10-40% EtOAc in hexanes

Sources & evidence

ORD record: ord-b7c5ce32c29f47359e30e3fdd583de49
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572922B2

Reaction notes

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