Dimethylformamide → HCID 67335402, compound

HRID 1669843Notes

Reaction equation

HRID 1669843 reaction equation
Br[C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[C:8]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[N:9][N: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]=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([C:8]2[C:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([C:31]#[N:32])=[CH:30][CH:29]=3)=[CH:11][N:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:20])([F:22])[F:21])=[CH:14][CH:13]=3)[N:9]=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 67336156HCID 67336156, compound

Product 1

HCID 67335402HCID 67335402, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
75 °C

Procedure

A mixture of 0.75 g 4-(4-bromobenzyl)-3-cyclohexyl-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazole from Step D Example 13, 110 mg zinc cyanide, and 90 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 colorless gel. 1H NMR (CDCl3, 500 MHz) δ 7.64˜7.65 (m, 2H), 7.62˜7.64 (m, 2H), 7.50 (s, 1H), 7.35 (d, J=8.2 Hz, 2H), 7.26˜7.29 (m, 2H), 3.94 (s, 2H), 2.58 (tt, J=3.1 & 11.9 Hz, 1H), 1.82˜1.87 (m, 4H), 1.72˜1.76 (m, 1H), 1.58˜1.67 (m, 2H), 1.28˜1.38 (m, 3H). LC-MS: 2.67 min. (M+H=426).

Workup

  1. customEvaporate most of DMF
  2. customThe residue was purified on silica gel using 10˜40% EtOAc in hexanes

Sources & evidence

ORD record
ord-ddf100980f9f445cb2b584e78d3e106b
Source dataset
uspto-grants-2011_08
Patent number
US07989475B2

Reaction notes

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