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Dimethylformamide → 4-[3-[Di(cyclopropylmethyl)amino]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-7-yl]-3-methoxybenzonitrile

HRID 9217
Notes
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Reaction equation

HRID 9217 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[N:14]=[C:15]([S:26][CH3:27])[C:16]([N:17]([CH2:22][CH:23]4[CH2:25][CH2:24]4)[CH2:18][CH:19]4[CH2:21][CH2:20]4)=[C:12]3[CH:11]=[CH:10][CH:9]=2)=[C:4]([O:28][CH3:29])[CH:3]=1.C(OCC)(=O)C.[CH3:36][N:37](C)C=O>[C-]#N.[Zn+2].[C-]#N>[CH:19]1([CH2:18][N:17]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[C:16]2[C:15]([S:26][CH3:27])=[N:14][N:13]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([C:36]#[N:37])=[CH:3][C:4]=4[O:28][CH3:29])=[CH:9][CH:10]=[CH:11][C:12]=23)[CH2:21][CH2:20]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 21984710N-[7-(4-bromo-2-methoxyphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N,N-dicyclopropylmethylamine

Product 1

HCID 219845664-[3-[Di(cyclopropylmethyl)amino]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-7-yl]-3-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 11186
Zinc cyanide (Zn(CN)2)
Catalyst

Conditions

Temperature
95 °C

Procedure

After dissolving N-[7-(4-bromo-2-methoxyphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N,N-dicyclopropylmethylamine (60 mg) in N,N-dimethylformamide (0.26 mL), zinc cyanide (31 mg) and tetrakis (triphenylphosphine)palladium (0) complex (23 mg) were added, the mixture was heated and stirred at 95° C. for 12 hours and then cooled to room temperature, and ethyl acetate was added. After filtering out the precipitated insoluble portion, extraction was performed with ethyl acetate. The obtained organic layer was washed with water and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:8) to obtain the title compound (32 mg) as a yellow oil.

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperaturecooled to room temperature
  4. filtrationAfter filtering out
  5. extractionthe precipitated insoluble portion, extraction
  6. washThe obtained organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:8)

Sources & evidence

ORD record
ord-47a5528724e2431dbb12cb455458e194
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091215B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes