Boron tribromide → HCID 56847984, compound

HRID 2093717Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][C:10]([C:12]2[C:13]([CH2:27][O:28]C)=[N:14][C:15]3[C:20]([C:21]=2[CH3:22])=[CH:19][CH:18]=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=3)=[O:11])[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.CCOC(C)=O.CCCCCC.CCOC(C)=O.C(Cl)Cl>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][C:10]([C:12]2[C:13]([CH2:27][OH:28])=[N:14][C:15]3[C:20]([C:21]=2[CH3:22])=[CH:19][CH:18]=[C:17]([C:23]([F:24])([F:25])[F:26])[CH:16]=3)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 220 mg (0.54 mmol) N-[(3-fluorophenyl)-methyl]-2-(methoxymethyl)-4-methyl-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide (Example 15) in DCM (5 ml) was cooled to −78° C. and 5.4 ml (5.4 mmol, 2M in DCM) boron tribromide was added. After heating to 0° C., the mixture was stirred for 16 h at this temperature. Quenching was then carried out with a 1M aq. NaHCO3 sol. (15 ml) and a 10%-strength aq. Na2S2O3 sol. It was then diluted with MeOH and DCM and the organic phase was separated, dried over MgSO4 and concentrated in a vacuum. After CC (EtOAc/hexane 1:1→EtOAc/DCM 1:1) of the residue, 110 mg (0.28 mmol, 52%) N-[(3-fluorophenyl)-methyl]-2-(hydroxy-methyl)-4-methyl-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide (example 17) was obtained. MS: m/z 393.1 [M+H]+.

Workup

customQuenching
additiona 10%-strength aq. Na2S2O3 sol. It was then diluted with MeOH and DCM
customthe organic phase was separated
dry with materialdried over MgSO4
concentrationconcentrated in a vacuum

Sources & evidence

ORD record: ord-1afe871badfe4010826d69a7be3955a2
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445512B2

Reaction notes

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