Boron tribromide → 4-(4-bromo-3-hydroxyphenyl)-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 525234Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][C@@H:14]3[CH2:18][CH2:17][N:16]([C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[CH2:15]3)=[N:11][NH:10][C:9]2=[O:24])=[CH:4][C:3]=1[O:25]C.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][C@@H:14]3[CH2:18][CH2:17][N:16]([C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[CH2:15]3)=[N:11][NH:10][C:9]2=[O:24])=[CH:4][C:3]=1[OH:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a round bottom flask, 4-[4-bromo-3-(methyloxy)phenyl]-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one (0.349 mmol) was dissolved in dichloromethane (3.5 mL) and cooled to 0° C. Boron tribromide (2.443 mmol) was added to the solution slowly, which was then allowed to warm to room temperature. The reaction was stirred for 1 h, and analysis by LCMS indicated complete conversion to desired product. The reaction was poured into a separatory funnel and partitioned with saturated aq sodium bicarbonate. The aqueous layer was extracted with dichloromethane (3×) and the combined organic layers were dried over Na2SO4, filtered, and concentrated to afford the title product as a tan solid (110 mg, 77%). MS(ES)+ m/e 407.1, 408.9 [M+H]+.

Workup

temperatureto warm to room temperature

Sources & evidence

ORD record: ord-b7570172d09b486ab61aeb20105ad847
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340529B2

Reaction notes

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