m-Chloroperbenzoic acid → Thieno[2,3-c]pyridine, 7-chloro-, 6-oxide

HRID 389524Notes

Reaction equation

HRID 389524 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][S:8][C:7]=12.ClC1C=CC=C(C(OO)=[O:19])C=1>C(Cl)Cl>[Cl:1][C:2]1[N+:3]([O-:19])=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][S:8][C:7]=12

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 159141297-Chlorothieno[2,3-c]pyridine

Product 1

HCID 86662415Thieno[2,3-c]pyridine, 7-chloro-, 6-oxideYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-chlorothieno[2,3-c]pyridine (5.00 g, 29.5 mmol) in DCM (200 mL) was added m-chloroperbenzoic acid (13.2 g, 59.0 mmol). The combined mixture was stirred at RT for 24 h. After that time, it was purified by ISCO chromatography (0 to 6% MeOH:DCM) to afford 3.18 g (58%) of the title compound as a light brown solid. 1H NMR (400 MHz, CDCl3): δ 8.31 (d, J=7.2 Hz, 1 H), 7.69 (d, J=5.2 Hz, 1 H), 7.57 (d, J=6.8 Hz, 1 H), 7.35 (d, J=5.2 Hz, 1 H); MS (ESI): 185.95, 187.96 [M+H]+; HPLC tR=0.88 min (TOF: polar—3 min).

Workup

  1. customAfter that time, it was purified by ISCO chromatography (0 to 6% MeOH:DCM)

Sources & evidence

ORD record
ord-47a6d8b19cb04e6c9afe6e12e86fcb34
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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