Boron tribromide → 3-(1H-Pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-ol

HRID 1991115Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:11]([C:12]3[CH:13]=[N:14][NH:15][CH:16]=3)=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[NH:14]1[CH:13]=[C:12]([C:11]2[C:5]3[C:6](=[N:7][CH:8]=[C:3]([OH:2])[CH:4]=3)[NH:9][CH:10]=2)[CH:16]=[N:15]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 35 (25 mg, 0.12 mmol) in CH2Cl2 (2.0 mL), cooled to 0° C., was added a 1M solution of BBr3 (467 μL, 0.48 mmol) in CH2Cl2 and the reaction mixture stirred for 2 h at room temperature. More CH2Cl2 (2.0 mL) and BBr3 (467 μL) was added at r.t. and the stirring continued for 65 h. The reaction mixture was partitioned between AcOEt and saturated aqueous NaHCO3 and the layers separated. The aqueous phase was extracted with more AcOEt (4×), the combined organic extracts dried (MgSO4) and concentrated. The residue was purified by preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—MeCN (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to give 36 as a white solid (9.1 mg, 39%); 1H NMR (400 MHz, DMSO-d6) δ 7.49 (d, J=2.5 Hz, 1H), 7.57 (d, J=2.5 Hz, 1H), 7.86 (d, J=2.5 Hz, 1H), 7.90 (s, 2H), 9.05-9.20 (bs, 1H), 11.32 (bs, NH).

Workup

waitthe stirring continued for 65 h
customThe reaction mixture was partitioned between AcOEt and saturated aqueous NaHCO3
customthe layers separated
extractionThe aqueous phase was extracted with more AcOEt (4×)
dry with materialthe combined organic extracts dried (MgSO4)
concentrationconcentrated
customThe residue was purified by preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record: ord-39addd2b77374396a78c110920a1f1c7
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645769B2

Reaction notes

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