Dimethylformamide → HCID 67334339, compound

HRID 2102221Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 651 mg 5-(4-bromobenzyl)-1-cyclohexyl-3-[4-(trifluoromethoxy)phenyl]-1H-pyrazole from Step C Example 11, 95.7 mg zinc cyanide, 62.9 mg tetrakis(triphenylphosphine)palladium(0) in 2.5 mL DMF was heated under nitrogen in 80° C. oil bath for 24 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 yellow foam. 1H NMR (CDCl3, 600 MHz) δ 7.78˜7.81 (m, 2H), 7.63 (d, J=8.3 Hz, 2H), 7.33 (d, J=8.2 Hz, 2H), 7.215 (d, J=8.3 Hz, 2H), 6.25 (s, 1H), 4.09 (s, 2H), 3.83 (tt, J=3.9 & 11.7 Hz, 1H), 1.96˜2.03 (m, 2H), 1.85˜1.89 (m, 2H), 1.73˜1.77 (m, 2H), 1.68˜1.71 (m, 1H), 1.23˜1.33 (m, 3H). LC-MS: 2.63 min. (M+H=426).

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-788e010a6e014720b18fb8cfd2127bbe
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572922B2

Reaction notes

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