Boron tribromide → HCID 178468892, compound

HRID 639391Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:32])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[C:19]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([O:30]C)[CH:24]=4)=[N:20][NH:21][CH:22]=3)[CH:15]=[CH:14][N:13]=2)[CH:6]=1)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:32])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[C:19]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([OH:30])[CH:24]=4)=[N:20][NH:21][CH:22]=3)[CH:15]=[CH:14][N:13]=2)[CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: -5 °C

Procedure

3-{4-[3-(4-Chloro-3-methoxy-phenyl)-1H-pyrazol-4-yl]-pyrimidin-2-ylamino}-benzoic acid ethyl ester (Example 41) (18 mg, 0.04 mmoles) is suspended in CH2Cl2 (2 mL) and cooled to −5° C. BBr3 (0.5 mL, 1M in CH2Cl2) is added dropwise at −5° C. After 10 min the suspension turns to a clear brown solution. After 2 h at −5° C. another 0.5 mL of BBr3 is added to the reaction mixture. Then the reaction mixture is warmed to rt and kept at that temperature for 30 min. The reaction is quenched with 5 mL water and stirred at rt overnight. The reaction mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, concentrated and chromatographed on SiO2 (80% EtOAc/Hexanes) affording the title compound: ES-MS 436.1178 [M+H]; single peak at tR=5.579 min (System 3).

Workup

temperatureThen the reaction mixture is warmed to rt
waitkept at that temperature for 30 min
customThe reaction is quenched with 5 mL water
extractionThe reaction mixture is extracted with ethyl acetate
dry with materialThe combined organic phases are dried over sodium sulfate
concentrationconcentrated
customchromatographed on SiO2 (80% EtOAc/Hexanes)

Sources & evidence

ORD record: ord-64d7b6c1f7604f5dab70e41ca7a4410d
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691855B2

Reaction notes

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