Methanol → HCID 90013475, compound

HRID 589011Notes

Reaction equation

HRID 589011 reaction equation
Br[C:2]1[C:7]([CH2:8][CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:22]([O-:25])(=[O:24])C.[Na+].[CH3:27]O>>[CH3:15][O:14][C:12](=[O:13])[CH2:11][O:10][CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][C:7]1[C:2]([C:22]([O:25][CH3:27])=[O:24])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 517045Sodium AcetateHCID 90013565HCID 90013565, compound

Product 1

HCID 90013475HCID 90013475, compound

Conditions

Temperature
23 °C

Procedure

A stream of CO gas was bubbled through a mixture of methyl 2-(2-(2-bromopyridin-3-yl)-1-phenylethoxy)acetate (6.5 g, 18 mmol), sodium acetate (4.6 g, 55 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (3.0 g, 3.7 mmol) in anhydrous methanol (650 mL) at 70° C. for 4 h. The reaction mixture was cooled to 23° C. and concentrated. The residue was dissolved ethyl acetate (200 mL) and filtered through Celite®. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in petroleum ether to give the title compound. MS: m/z=330.2 (M+1).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved ethyl acetate (200 mL)
  3. filtrationfiltered through Celite®
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-79baedf9ee1949288a597c13e9d03985
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

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