Methanol → HCID 58294454, compound

HRID 520993Notes

Reaction equation

HRID 520993 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

Conditions

Temperature
80 °C

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° C. 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. temperatureAfter cooling to room temperature
  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-6ec74011946649c9a46cd60dd94d5242
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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