1H-pyrrolo[2,3-b]pyridine, 5-chloro-, 7-oxide synthesis
- Product Name:1H-pyrrolo[2,3-b]pyridine, 5-chloro-, 7-oxide
- CAS Number:916176-51-7
- Molecular formula:C7H5ClN2O
- Molecular Weight:168.58
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Yield:916176-51-7 63.4%
Reaction Conditions:
with 3-chloro-benzenecarboperoxoic acid in dichloromethane at 0 - 20;
Steps:
4.1 Step 1) 5-chloro-lH-pyrrolo[2.3-&]pyridine oxide
To a solution of 5-chloro-lH-pyrrolo[2,3-6]pyridine (20.00 g, 131.1 mmol) in dichloromethane (500 mL) was added mCPBA (85% [w/w], 67.86 g, 393.2 mmol) at 0 °C. The reaction mixture was allowed to rt and stirred overnight and concentrated in vacuo. The residue was dissolved in water (250 mL) and the resulting mixture was adjusted to pH = 8-9 with a saturated Na2C03aqueous solution, then extracted with DCM (250 mLχ3). The combined organic phases were washed with brine (250 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v) = 1/50) to give the title compound as a gray solid (14.00 g, yield 63.4%). MS (ESI, pos. ion) m/z: 169.1 [M+H]+; MR (400 MHz, DMSO-t) δ (ppm): 12.69 (s, 1H), 8.36 (d, J= 1.4 Hz, 1H), 7.80 (d, J= 1.4 Hz, 1H), 7.53 (d, 7= 2.8 Hz, 1H), 6.56 (d, 7= 3.1 Hz, 1H).
References:
WO2018/169700,2018,A1 Location in patent:Paragraph 00328
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