Dimethylformamide → 6-Formyl-4-methoxy-quinoline-3-carboxylic acid dimethylamide

HRID 1297624Notes

Reaction equation

HRID 1297624 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][C:11](I)=[CH:10][CH:9]=2)=[O:4].C1(C(C2C=CC=CC=2)CCP)C=CC=CC=1.C([SiH](CCCCCC)CCCCCC)CCCCC.CN(C)[CH:56]=[O:57]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][N:2]([CH3:18])[C:3]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][C:11]([CH:56]=[O:57])=[CH:10][CH:9]=2)=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 76231CID 76231HCID 53436545Diphenylpropyl phosphineHCID 585858426-Iodo-4-methoxy-quinoline-3-carboxylic acid dimethylamide

Product 1

HCID 585857826-Formyl-4-methoxy-quinoline-3-carboxylic acid dimethylamide

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A mixture of 6-iodo-4-methoxy-quinoline-3-carboxylic acid dimethylamide (example 10b) (1.27 g, 3.57 mmol), trethylamine (1.23 mL, 8.93 mmol), diphenylpropylphosphine (dpp, 81 uL, 0.36 mmol) and palladium(II) acetate (80 mg, 0.36 mmol) in dry N,N-dimethylformamide (20 mL) in pressure tube was stirred under carbon monoxide at 75 psi at room temperature for 10 min. After addition of trihexylsilane (2.54 mL, 7.14 mmol), the mixture was then stirred under carbon monoxide at 75 psi at 80° C. for 3 h. The reaction was allowed to cool to 25° C. and then extracted with methylene chloride (2×100 mL). The combined organic layers were successively washed with a saturated aqueous sodium bicarbonate solution (3×50 mL) and water (3×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-40% ethyl acetate in hexanes in 30 min) afforded 6-formyl-4-methoxy-quinoline-3-carboxylic acid dimethylamide as a white solid. LC-MS m/e 259 (MH+).

Workup

  1. stirringthe mixture was then stirred under carbon monoxide at 75 psi at 80° C. for 3 h
  2. temperatureto cool to 25° C.
  3. extractionextracted with methylene chloride (2×100 mL)
  4. washThe combined organic layers were successively washed with a saturated aqueous sodium bicarbonate solution (3×50 mL) and water (3×50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57b6d80a7f1d477da59ab81418284560
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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