Methanol → HCID 58294454, compound
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
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
- customis flushed with argon for 5 min and with carbon monoxide for another 5 min
- temperatureAfter cooling to room temperature
- filtrationthe mixture is filtered
- concentrationconcentrated under reduced pressure
- washwashed with water and brine
- dry with materialdried (Na2SO4)
- customThe solvent is evaporated
- customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→0:1)
Sources & evidence
- ORD record
- ord-fad008e64d904104a9ab3b0fcbce25d7
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120769B2
Reaction notes
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