Allyl Alcohol → 3-(6-Isopropylaminopyridin-3-yl)propionaldehyde

HRID 734902Notes

Reaction equation

I[C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]([CH3:11])[CH3:10])=[N:6][CH:7]=1.[CH2:12]([OH:15])[CH:13]=[CH2:14].C(=O)([O-])O.[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.O.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:9]([NH:8][C:5]1[N:6]=[CH:7][C:2]([CH2:14][CH2:13][CH:12]=[O:15])=[CH:3][CH:4]=1)([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1.80 g (6.87 mmol) of (5-iodopyridin-2-yl)isopropylamine, 1.40 mL (10.7 mmol) of prop-2-en-1-ol, 1.39 g (16.49 mmol) of sodium hydrogen carbonate, 1.72 g (6.18 mmol) of tetrabutylammonium chloride, and 46 mg (0.20 mmol) of palladium (II) acetate in 10 mL of DMF was stirred under argon for 20 hours at 50° C. The reaction mixture was diluted with water and EtOAc, the organic phase was separated off, washed several times with water, and dried over magnesium sulfate. After the desiccant and solvent had been eliminated, the residue was purified by chromatography (silica gel, PE/EtOAc 1:1). Yield: 300 mg (23% of theoretical); ClIH16N2O (M=192.258); calc.: molpeak (M+H)+:193; found: molpeak (M+H)+:193; HPLC-MS: 3.58 minutes (method G).

Workup

customthe organic phase was separated off
washwashed several times with water
dry with materialdried over magnesium sulfate
customthe residue was purified by chromatography (silica gel, PE/EtOAc 1:1)
custom3.58 minutes (method G)

Sources & evidence

ORD record: ord-4aefb381620f4cb9a07ccf2d2d9b5b7b
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592358B2

Reaction notes

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