Boron tribromide → 2-[6-(Dimethylamino)pyridin-3-yl]-1,3-benzoxazol-5-ol

HRID 2241808Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([N:17]([CH3:19])[CH3:18])=[N:15][CH:16]=3)=[N:8][C:7]=2[CH:20]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>ClCCl>[CH3:18][N:17]([CH3:19])[C:14]1[N:15]=[CH:16][C:11]([C:9]2[O:10][C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:20][C:7]=3[N:8]=2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(5-methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyridin-2-amine (0.368 mmol) in dichloromethane (2.0 mL) was added BBr3 in dichloromethane (1.84 mmol) at 0° C. under an atmosphere of argon and the reaction stirred for 1 h at 0° C. The reaction mixture was neutralized with NaHCO3 (sat. aq.) and dichloromethane was added. The layers were separated and the aqueous phase was extracted with dichloromethane (4×). The combined organic phases were dried (MgSO4), filtered and the solvents removed in vacuo. The crude material was purified by preparative HPLC to give 22.3 mg of the title compound as a white solid. 1H NMR δ ppm 9.44 (s, 1H), 8.83 (d, 1H), 8.13 (dd, 1H), 7.48 (d, 1H), 7.01 (d, 1H), 6.80 (d, 1H), 6.76 (dd, 1H), 3.14 (s, 6H). MS m/z (M+H) 256.

Workup

additionwas added
customThe layers were separated
extractionthe aqueous phase was extracted with dichloromethane (4×)
dry with materialThe combined organic phases were dried (MgSO4)
filtrationfiltered
customthe solvents removed in vacuo
customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record: ord-52538839318447f79a7015f49c633089
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07670591B2

Reaction notes

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