Dimethylacetamide → HCID 66665839, compound

HRID 872340Notes

Reaction equation

HRID 872340 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[C:25](Br)=[CH:24][C:23]([Cl:27])=[CH:22][N:21]4[C:28]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][N:37](C)C(=O)C>C(OCC)(=O)C.[Zn].[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[C:25]([C:36]#[N:37])=[CH:24][C:23]([Cl:27])=[CH:22][N:21]4[C:28]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 31374DimethylacetamideHCID 66665078HCID 66665078, compound

Product 1

HCID 66665839HCID 66665839, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst2×HCID 23994ZincCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

300 mg (0.54 mmol) {1-[4-(8-Bromo-6-chloro-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester, intermediate example Int-400-12, 3.5 mg (0.054 mmol) zinc, 44.3 mg (0.054 mmol) 1,1 bis(diphenylphosphino)-ferrocenedichloropalladium(II) and 127.4 mg (1.08 mmol) zinc cyanide in 4.5 mL N,N-dimethylacetamide (degassed) were heated in the microwave at 110° C. for three hours. Due to an incomplete reaction additional zinc, catalyst and zinc cyanide were added, and stirring was continued at 150° C. for one hour. The reaction mixture was diluted with ethyl acetate and washed with water/saturated ammonium chloride. The organic phase was separated, dried (sodium sulfate), filtrated and the solvent was removed. The crude product (530 mg >100%) was used in the next step without further purification.

Workup

  1. customwere heated in the microwave at 110° C. for three hours
  2. washwashed with water/saturated ammonium chloride
  3. customThe organic phase was separated
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltrated
  6. customthe solvent was removed
  7. customThe crude product (530 mg >100%) was used in the next step without further purification

Sources & evidence

ORD record
ord-cb6d9761195744a6b384c54d9715968e
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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