Boron tribromide → HCID 136164946, compound

HRID 1862141Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

3-1H-Benzoimidazol-2-yl-6-(2-(2-methoxyethyl)-4-hydroxyphenyl)-1H-indazole, from Example 24(i), (99 mg, 0.26 mmol) was dissolved in EtOAc (20 mL) and cooled to −78° C. under argon. Boron tribromide was added dropwise, and the reaction was allowed to stir while warming to r.t over 3 h. The solution was diluted with EtOAc (60 mL) and washed with sat NaHCO3 and brine (20 mL each). Organics were dried (Na2SO4) and concentrated in vacuo. Purification by silica gel chromatography (THF) gave 56 mg (59%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 13.60 (s, 1H), 13.01 (s, 1H), 9.41 (s, 1H), 8.49 (d, 1H, J=8.4 Hz), 7.71 (br s, 1H), 7.51 (br s, 1H), 7.46 (s, 1H), 7.21 (app d, 3H, J=8.1 Hz), 7.08 (d, 1H, J=8.4 Hz), 6.77 (d, 1H, J=2.1 Hz), 6.69 (dd, 1H, J=8.1, 2.1 Hz), 4.57 (br s, 1H), 3.46 (t, 2H, J=7.2 Hz), 2.68 (t, 2H, J=7.2 Hz). MS (ES) [m+H]/z calc'd 371, found 371; [m−H]/z calc'd 369, found 369.

Workup

temperaturewhile warming
washwashed
dry with materialOrganics were dried (Na2SO4)
concentrationconcentrated in vacuo
customPurification by silica gel chromatography (THF)

Sources & evidence

ORD record: ord-4edd30076abe472198cee7ed860740d2
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06534524B1

Reaction notes

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