Boron tribromide → HCID 59402776, compound

HRID 538562Notes

Reaction equation

[F:1][C:2]1[C:10]([O:11][CH2:12][C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=3)[N:17]=2)=[CH:9][CH:8]=[C:7]([F:26])[C:3]=1[C:4]([NH2:6])=[O:5].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[C:10]([O:11][CH2:12][C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[N:17]=2)=[CH:9][CH:8]=[C:7]([F:26])[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2,6-Difluoro-3-[4-(4-methoxy-phenyl)-thiazol-2-ylmethoxy]-benzamide (0.20 g, 0.53 mmol) in 15 ml of DCM was cooled to −78° C. followed by addition of BBr3 (0.2 ml, 2.14 mmol). The reaction mixture was stirred at 25° C. for 2 h. After the completion of the reaction mixture (TLC monitoring), solution of NaHCO3 (20 mL) was added at 0° C. and extracted with ethyl acetate (3×50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated, the residue was purified by column chromatography on silica (60-120 M) using ethyl acetate/hexane (50:50) as the eluent to provide the title compound as light yellow solid (0.06 g, 31%). 1H NMR (DMSO-d6, 400 MHz): δ 5.55 (s, 2H), 6.83 (d, J=8.40 Hz, 2H), 7.13 (m, 1H), 7.40 (m, 1H), 7.78 (d, J=8.80 Hz, 2H), 7.88 (br s, 1H), 7.91 (s, 1H), 8.17 (br s, 1H) and 9.64 (br s, 1H). MS ES+ (363.25), HPLC (method I) Rt=14.57 min.

Workup

extractionextracted with ethyl acetate (3×50 mL)
washThe combined organics was washed with water, brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customthe residue was purified by column chromatography on silica (60-120 M)

Sources & evidence

ORD record: ord-9690ff0149b7426d9df63337692821c4
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865736B2

Reaction notes

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