Boron tribromide → 2,6-Dimethyl-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenol

HRID 1177568Notes

Reaction equation

B(Br)(Br)Br.C([O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([C:20]2[S:21][C:22]3[C:27]([N:28]=2)=[CH:26][CH:25]=[C:24]([C:29]2([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH2:31][CH2:30]2)[N:23]=3)=[CH:15][C:14]=1[CH3:38])C1C=CC=CC=1>C(Cl)Cl>[CH3:38][C:14]1[CH:15]=[C:16]([C:20]2[S:21][C:22]3[C:27]([N:28]=2)=[CH:26][CH:25]=[C:24]([C:29]2([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:30][CH2:31]2)[N:23]=3)[CH:17]=[C:18]([CH3:19])[C:13]=1[OH:12]

Participants

Conditions

Temperature: -78 °C

Procedure

Boron tribromide (1.0M in DCM; 963 μl, 0.963 mmol) was added to a solution of 2-(4-(benzyloxy)-3,5-dimethylphenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (247.4 mg, 0.535 mmol) in DCM (24.0 mL) at −78° C., and the resulting solution was stirred at −78° C. for 5 min. Excess BBr3 was then quenched by the addition of water (50 mL), and the resulting mixture was diluted with DCM (100 mL) and allowed to warm to 25° C. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-100% ethyl ether/hexanes) afforded 2,6-dimethyl-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenol as a white solid. MS (ESI) m/z: Calculated: 372.1; Observed: 373.2 (M++1).

Workup

customExcess BBr3 was then quenched by the addition of water (50 mL)
additionthe resulting mixture was diluted with DCM (100 mL)
temperatureto warm to 25° C
customThe organic layer was separated
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customChromatographic purification of the residue (silica gel, 0-100% ethyl ether/hexanes)

Sources & evidence

ORD record: ord-73503888c33c4f5098b1a99285f78ea3
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

Loading…