Boron tribromide → HCID 25212304, compound

HRID 1409857Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:11]1[S:12][C:13]([C:16]2[C:20]([CH3:21])=[C:19]([C:22]([F:25])([F:24])[F:23])[O:18][N:17]=2)=[CH:14][CH:15]=1)=[O:10].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:11]1[S:12][C:13]([C:16]2[C:20]([CH3:21])=[C:19]([C:22]([F:25])([F:24])[F:23])[O:18][N:17]=2)=[CH:14][CH:15]=1)=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (2-methoxyphenyl){5-[4-methyl-5-(trifluoromethyl)isoxazol-3-yl]thien-2-yl}methanone (Example 95, 37 mg, 0.1 mmol) in dichloromethane (2 mL) at −78° C. was treated with boron tribromide (100 μL of a 1 M dichloromethane solution, 0.1 mol) and allowed to warm to 0° C. and stir at that temperature for 16 h. After that time the reaction was quenched with water (3 mL) and partitioned between water (10 mL) and EtOAc (10 mL). The organic extract was washed with a brine solution (10 mL) then dried over Na2SO4, filtered, and concentrated in vacuo to afford crude product. The crude product was chromatographed on silica gel with EtOAc/hexanes (20%) as eluant to afford product as a yellow colored solid (29 mg, 82%). 1H NMR (CDCl3) 2.92 (d, J=1.8, 3 H), 7.46-7.76 (m, 2 H), 8.03-8.08 (m, 1 H), 8.12 (d, J=4.0, 1 H), 8.28 (d, J=4.0, 1 H), 8.46 (dd, J=8.4, 1.8, 1 H), 11.50 (s, 1 H). 19F NMR −63.1.

Workup

customAfter that time the reaction was quenched with water (3 mL)
custompartitioned between water (10 mL) and EtOAc (10 mL)
extractionThe organic extract
washwas washed with a brine solution (10 mL)
dry with materialthen dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customto afford crude product
customThe crude product was chromatographed on silica gel with EtOAc/hexanes (20%) as eluant

Sources & evidence

ORD record: ord-49bbca2a2ff74a5eb408a9a6336378b7
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921399B2

Reaction notes

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