Dimethylformamide → HCID 21697001, compound

HRID 379054Notes

Reaction equation

HRID 379054 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)([C:10]2[N:11]=[CH:12][N:13]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:14]=2)[OH:9])=[CH:4][C:3]=1F.[CH3:42][N:43](C=O)C>CCOC(C)=O.[C-]#N.[C-]#N.[Zn+2].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>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([C:8]([OH:9])([C:10]2[N:11]=[CH:12][N:13]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:14]=2)[C:5]2[CH:6]=[CH:7][C:2]([C:42]#[N:43])=[CH:3][CH:4]=2)=[CH:35][CH:36]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 21696984HCID 21696984, compound

Product 1

HCID 21697001HCID 21697001, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst2×HCID 178418397HCID 178418397, compoundCatalyst2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

(4-Bromo-3-fluoro-phenyl)-(4-chloro-phenyl)-(1-trityl-1H-imidazol-4-yl)-methanol (0.360 g, 0.578 mmol) and Zn(CN)2 (0.045 g, 0.405 mmol) was stirred in anhydrous DMF (8 mL). The solution was purged with Ar for 10 min, degassed under high vacuum for 5 min, then tetrakis(triphenylphosphine)palladium(0) (0.067 mg, 0.057 mmol) was added and the mixture stirred overnight at 80° C. under Ar. Subsequent additions of Zn(CN)2 and tetrakis(triphenylphosphine)palladium(0) were added to drive the reaction to completion. The reaction was diluted with EtOAc and extracted with satd. NaHCO3 solution, water and brine, dried (MgSO4), concentrated and purified using SiO2 chromatography (0.5% MeOH/CH2Cl2) to yield the title compound.

Workup

  1. customThe solution was purged with Ar for 10 min
  2. customdegassed under high vacuum for 5 min
  3. customthe reaction to completion
  4. extractionextracted with satd
  5. dry with materialNaHCO3 solution, water and brine, dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-c771560a4cdb4197989fcd0b2b0a6b1c
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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