Boron tribromide → 2-(7-Amino-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-phenol

HRID 1802274Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:18]=[C:12]2[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][N:11]2[N:10]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:17][C:14]1[CH:15]=[CH:16][N:11]2[N:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[OH:2])[N:18]=[C:12]2[CH:13]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine (2.3 g, 9.6 mmol) (Example 102, step c) in DCM (60 ml) was added a solution of BBr3 (1 M in DCM, 28.7 ml, 28.7 mmol). The mixture was allowed to warm up to 25° C. and stirring was continued for 2 h. Volatiles were removed under reduced pressure and the crude residue was extracted with DCM and washed with aq. NaHCO3 solution. The organic layer was washed with brine, dried over Na2SO4 and concentrated to get the crude product which was washed with 10% DCM in hexane to afford the title compound as off-white solid (1.3 g, 60%). LC-MS: m/z=227.4 [M+H]+.

Workup

customVolatiles were removed under reduced pressure
extractionthe crude residue was extracted with DCM
washwashed with aq. NaHCO3 solution
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customto get the crude product which
washwas washed with 10% DCM in hexane

Sources & evidence

ORD record: ord-89327fe6c6de412b9fb37259b93d66bf
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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