Dimethylformamide → HCID 58368632, compound

HRID 1192571Notes

Reaction equation

HRID 1192571 reaction equation
Br[C:2]1[CH:11]=[C:10]([CH:12]=[O:13])[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:21][N:22](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>[F:20][C:16]1[CH:15]=[C:14]([C:9]2[C:8]3[N:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:2]([C:21]#[N:22])=[CH:11][C:10]=2[CH:12]=[O:13])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 58368654HCID 58368654, compound

Product 1

HCID 58368632HCID 58368632, compoundYield 50%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
130 °C

Procedure

A mixture of 5-bromo-8-(3-fluorophenyl)quinoline-7-carbaldehyde (0.049 g, 0.15 mmol), zinc cyanide (0.035 g, 0.30 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.034 g, 0.030 mmol) in dry N,N-dimethylformamide (0.50 mL) was stirred at 130° C. overnight. The mixture was filtered, diluted with water, extracted with ethyl acetate. The combined extracts were dried over MgSO4, concentrated and purified on silica gel (eluting with 0 to 60% ethyl acetate in hexane) to give the desired product (20 mg, 50%). LCMS calculated for C17H10FN2O (M+H)+: m/z=277.1; Found: 277.0.

Workup

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

Sources & evidence

ORD record
ord-709b0442fcfc45d89e8661c47037c40c
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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