Dimethylformamide → HCID 67335072, compound

HRID 1669832Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 526 mg 3-(4-bromobenzyl)-1-cyclohexyl-5-[4-(trifluoromethoxy)phenyl]-1H-pyrazole from Step C above, 79.9 mg zinc cyanide, 50.8 mg tetrakis(triphenylphosphine)palladium(0) in 2 mL DMF was heated under nitrogen in 80° C. oil bath for 20 hours. Evaporate most of DMF. The residue was purified on silica gel using 1 and 3% MeCN in methylene chloride to give the title compound as a yellowish solid. 1H NMR (CDCl3, 500 MHz) δ 7.61 (d, J=8.2 Hz, 2H), 7.42 (d, J=8.3 Hz, 2H), 7.35˜7.38 (m, 2H), 7.31 (d, J=8.3 Hz, 2H), 5.94 (s, 1H), 4.09 (s, 2H), 4.02 (tt, J=2.75 & 11.7 Hz, 1H), 2.03˜2.11 (m, 2H), 1.87˜1.94 (m, 4H), 1.69˜1.72 (m, 1H), 1.25˜1.35 (m, 3H). LC-MS: 2.55 min. (M+H=426.2).

Workup

customEvaporate most of DMF
customThe residue was purified on silica gel using 1 and 3% MeCN in methylene chloride

Sources & evidence

ORD record: ord-d683b01c9aa14561a0da397c0bdd6a44
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989475B2

Reaction notes

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