Methanol → HCID 58294454, compound

HRID 2360764Notes

Reaction equation

HRID 2360764 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]2[C:6]3[CH:7]=[CH:8][CH:9]=[N:10][C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=1.C(N(CC)CC)C.CN(C)[CH:25]=[O:26].[CH3:28][OH:29]>>[CH3:28][O:29][C:25]([C:2]1[CH:15]=[CH:14][C:5]2[C:6]3[CH:7]=[CH:8][CH:9]=[N:10][C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=1)=[O:26]

Participants

5

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 58294389HCID 58294389, compound

Product 1

HCID 58294454HCID 58294454, compound

Procedure

A flask charged with 8-bromo-5,6-dihydro-benzo[f]quinoline (4.00 g), triethylamine (3.0 mL), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (0.63 g), N,N-dimethylformamide (5 mL), and methanol (20 ml) is flushed with argon for 5 min and with carbon monoxide for another 5 min. The mixture is then heated to 80 cc under carbon monoxide atmosphere (4 bar) and shaken at this temperature overnight. After cooling to room temperature, the mixture is filtered and concentrated under reduced pressure. The residue is taken up in ethyl acetate and washed with water and brine and dried (Na2SO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1) to afford the title compound as a solid. Yield: 3.16 g (86% of theory); LC (method 1): tR=2.18 min; Mass spectrum (ESI+): m/z=240 [M+H]+.

Workup

  1. customis flushed with argon for 5 min and with carbon monoxide for another 5 min
  2. temperatureThe mixture is then heated to 80 cc under carbon monoxide atmosphere (4 bar)
  3. filtrationthe mixture is filtered
  4. concentrationconcentrated under reduced pressure
  5. washwashed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customThe solvent is evaporated
  8. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1)

Sources & evidence

ORD record
ord-8b66b5eeb2744c7083af55465b9210c5
Source dataset
uspto-grants-2014_04
Patent number
US08686149B2

Reaction notes

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