Dimethylformamide → HCID 67215504, compound

HRID 472916Notes

Reaction equation

HRID 472916 reaction equation
Br[C:2]1[N:3]=[C:4]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([O:22][CH3:23])[CH:14]=2)=[O:12])[N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.[CH3:24][N:25](C)C=O>[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>[CH3:23][O:22][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[N+:19]([O-:21])=[O:20])[C:11]([C:4]1[N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]2=[C:2]([C:24]#[N:25])[N:3]=1)=[O:12]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 67215796HCID 67215796, compound

Product 1

HCID 67215504HCID 67215504, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

2.17 g (18.48 mmol) of zinc cyanide and then 1.07 g (0.93 mmol) of tetrakis(triphenylphosphine)palladium(0) are added under a nitrogen atmosphere to 6.94 g (18.45 mmol) of (1-bromoimidazo[1,5-a]pyridin-3-yl)(3-methoxy-4-nitrophenyl)methanone obtained in example 20 in 160 ml of N,N-dimethylformamide. The reaction medium is heated at 90° C. for 17 h. The precipitate obtained is filtered off, washed with water, then with a saturated aqueous sodium bicarbonate solution and with water. After drying, 5.9 g of a yellow solid are collected. Melting point: 219° C.; 1H NMR (d6-DMSO): 4.01 (3H, s), 7.53-7.55 (1H, m), 7.76-7.81 (1H, m), 7.95-8.01 (2H, m), 8.08 (1H, d), 8.19 (1H, d), 9.70 (1H, d)

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered off
  3. washwashed with water
  4. customAfter drying
  5. custom5.9 g of a yellow solid are collected

Sources & evidence

ORD record
ord-ec214a6fa15e45bbb4e44db6b56b5f13
Source dataset
uspto-grants-2014_01
Patent number
US08633216B2

Reaction notes

Loading…