Dimethylformamide → HCID 14770845, compound

HRID 1651577Notes

Reaction equation

HRID 1651577 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]3=[O:24])[CH2:10]2)=[C:4]([F:25])[CH:3]=1.[Cu][C:27]#[N:28].CN(C)C=O.[OH-].[NH4+]>O>[O:23]=[C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:24])[N:14]1[CH:11]1[CH2:12][CH2:13][CH:9]([C:5]2[C:4]([F:25])=[CH:3][C:2]([C:27]#[N:28])=[C:7]([F:8])[CH:6]=2)[CH2:10]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 14770834HCID 14770834, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 14770845HCID 14770845, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 91.35 g (0.225 mol) of 2-[3-(4-bromo-2,5-difluorophenyl)cyclopentyl]-1H-isoindole-1,3-(2H)-dione, 22.4 g (0.25 mol) of copper (I) cyanide and 250 ml of N,N-dimethylformamide was stirred and heated in a nitrogen atmosphere at 170° for 18 hours. The cooled mixture was poured into a solution of 100 ml of concentrated ammonium hydroxide in 1 L of water. The aqueous mixture was extracted with ether (4×350 ml) and the combined ether layers were washed with water (3×300 ml), dried (MgSO4), and evaporated in vacuo to give 71.2 g of the title compound which was used as is for the next step.

Workup

  1. temperatureheated in a nitrogen atmosphere at 170° for 18 hours
  2. extractionThe aqueous mixture was extracted with ether (4×350 ml)
  3. washthe combined ether layers were washed with water (3×300 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-9899f864b9cb458b875e3298111322ad
Source dataset
uspto-grants-1990_05
Patent number
US04929613

Reaction notes

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