m-Chloroperbenzoic acid → tert-butyl 6-chloro-8-(phenylsulfinyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

HRID 2179436Notes

Reaction equation

HRID 2179436 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C:10]=3[C:6]=2[CH:5]=[C:4]([S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:34]>ClCCl>[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C:10]=3[C:6]=2[CH:5]=[C:4]([S:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:34])[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68109020tert-butyl 6-chloro-8-(phenylthio)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

Product 1

HCID 68109176tert-butyl 6-chloro-8-(phenylsulfinyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylateYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the product of Example 91, step A (50 mg, 0.12 mmol) in dichloromethane (2.0 mL) at −10° C. was added a solution of m-chloroperoxybenzoic acid (18 mg, 0.108 mmol) in dichloromethane (1.0 mL) drop wise. The reaction mixture was stirred at ambient temperature for 2 h, concentrated in vacuo and purified by column chromatography (SiO2, 4:1 hexanes/ethyl acetate) providing tert-butyl 6-chloro-8-(phenylsulfinyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (30 mg, 58%) as an off-white solid: 1H NMR (CDCl3, 400 MHz) δ 7.68-7.63 (m, 3H), 7.51-7.45 (m, 4H), 4.55 (s, 2H), 3.86-3.77 (m, 2H), 2.93-2.85 (m, 2H), 1.50 (s, 9H).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by column chromatography (SiO2, 4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-2a42a64845394a128d421dab4876f2d2
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

Loading…