Boron tribromide → HCID 135511912, compound

HRID 859027Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([O:15][C:16]2[CH:25]=[C:24]3[C:19]([CH:20]=[CH:21][CH:22]=[N:23]3)=[CH:18][CH:17]=2)[CH:10]=1.B(Br)(Br)Br>ClCCl>[N:23]1[C:24]2[C:19](=[CH:18][CH:17]=[C:16]([O:15][C:11]3[N:12]=[CH:13][N:14]=[C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[OH:2])[CH:10]=3)[CH:25]=2)[CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a 50-mL, round-bottomed flask containing 7-[6-(2-methoxy-phenyl)-pyrimidin-4-yloxy]-quinoline, (Example 109), (0.09 g, 0.27 mmol) was added dichloromethane (3 mL). The solution was cooled to −78° C. and BBr3 (0.82 mL, 0.82 mmol, 1 N in dichloromethane, Aldrich) was added. The reaction mixture was allowed to warm to room temperature over 1 h and then cooled to −78° C. and quenched with satd sodium bicarbonate (10 mL). The reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (2×100 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuum. The resulting solid was suspended in methanol (15 mL) and the remaining solid was collected by filtration, and dried under vacuum to obtain the title compound as a white solid. Mp: 188–191° C. MS (ESI, pos. ion.) m/z: 316 (M+1).

Workup

temperatureto warm to room temperature over 1 h
temperaturecooled to −78° C.
customquenched with satd sodium bicarbonate (10 mL)
additionThe reaction mixture was diluted with water (50 mL)
extractionextracted with dichloromethane (2×100 mL)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated in vacuum
filtrationthe remaining solid was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-a472d6be8f334cd789dee5600939a65f
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148221B2

Reaction notes

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