Dimethylformamide → HCID 18779777, compound

HRID 1421715Notes

Reaction equation

HRID 1421715 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]4=[O:27])=[CH:17][CH:16]=3)[CH:12]=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:28][N:29](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>[C:28]([C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]4=[O:27])=[CH:17][CH:16]=3)[CH:12]=[N:11][CH:10]=2)=[CH:4][CH:3]=1)#[N:29]

Participants

5

Reactant 2

HCID 6228Dimethylformamide2×HCID 18779748HCID 18779748, compound

Product 1

HCID 18779777HCID 18779777, compound

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 1-{4-[5-(4-bromophenyloxy)imidazol-1-ylmethyl]-phenyl}-1H-pyridin-2-one (145 mg, 0.35 mmol) and zinc cyanide (24 mg, 0.2 mmol) in DMF (3 mL) was purged with argon for 10 min. A solution of tetrakis(triphenylphosphine)palladium(0) (40 mg, 35 μmol) in DMF (1 mL) was added. The resultant mixture was stirred under argon at 80° C. overnight, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 1:1 v/v 5% methanol in chloroform and chloroform saturated with ammonia gas. Collection and concentration of appropriate fractions provide the titled compound as white solid.

Workup

  1. customwas purged with argon for 10 min
  2. concentrationconcentrated under vacuum
  3. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-a4b0194161c84a46b9ed6477d4e4ba29
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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