Dimethylformamide → HCID 58368600, compound

HRID 1192582Notes

Reaction equation

HRID 1192582 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:4]([C:19](=[O:21])[CH3:20])[N:3]=1.[CH3:22][N:23](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>[C:19]([C:4]1[N:3]=[C:2]([C:22]#[N:23])[C:11]2[C:6]([C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2)(=[O:21])[CH3:20]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 58368661HCID 58368661, compound

Product 1

HCID 58368600HCID 58368600, compoundYield 6%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
130 °C

Procedure

A mixture of 1-[1-chloro-4-(3-fluorophenyl)isoquinolin-3-yl]ethanone (100 mg, 0.334 mmol), zinc cyanide (78 mg, 0.66 mmol) and tetrakis(triphenylphosphine)palladium(0) (77 mg, 0.067 mmol) in dry N,N-dimethylformamide (1.1 mL) was stirred at 130° C. overnight. The mixture was filtered, diluted with water, extracted with dichloromethane. The combined extracts were dried over MgSO4, concentrated and purified on silica gel (0-60% ethyl acetate in hexane) to give the desired product (6 mg, 6%). LCMS calculated for C18H12FN2O (M+H)+: m/z=291.1; Found: 291.1.

Workup

  1. filtrationThe mixture was filtered
  2. additiondiluted with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined extracts were dried over MgSO4
  5. concentrationconcentrated
  6. custompurified on silica gel (0-60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-98c42428d3f7409f9d6bfa9a0ae987ec
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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