Boron tribromide → HCID 9840680, compound

HRID 2119501Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:17]C)[CH:14]=3)[CH:9]2[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26]CCC3CCCCN3)=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:17])[CH:14]=3)[CH:9]2[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of 2-(4-fluorophenyl)-5-methoxy-1-{4-[(2-piperidyl)ethoxy]benzyl}isoindoline (0.14 g, 0.3 mmol) in CH2Cl2 (8 mL) under nitrogen at −10° C. was added a 1.0 M solution of boron tribromide in CH2Cl2 (0.6 mL, 0.6 mmol) dropwise. After stirring at −10° C. for 1hour, the reaction was quenched with ice and saturated sodium bicarbonate, then extracted with methylene choride. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was then purified by HPLC (C-18 column, 10-100% acetonitrile/water with 0.1% trifluoroacetic acid) to provide the title compound (0.084 g, 84% yield): 1H NMR (DMSO-d6) 7.04 (t, 2H), 6.88 (d, 1H), 6.69 (dd, 1H), 6.61-6.65 (m, 5H), 6.56 (d, 1H), 5.21 (m, 1H), 4.67 (s, 1H), 4.51 (s, 1H), 4.29 (d 1H), 4.10 (dd, 1H), 3.00-3.14 (m, 2H); ES−MS (m/z) 336 [M+H]+.

Workup

customthe reaction was quenched with ice and saturated sodium bicarbonate
extractionextracted with methylene choride
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was then purified by HPLC (C-18 column, 10-100% acetonitrile/water with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-3f18f7beac86446a946eb23576994f06
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06686351B2

Reaction notes

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