Hydrochloric Acid → 8-(4-Methoxyphenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride

HRID 2179320Notes

Reaction equation

HRID 2179320 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:24][C:23]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][C:18]=4[C:16]=3[CH:17]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[ClH:32]>ClCCl.CO.C(OCC)C>[ClH:32].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:24][C:23]4[CH2:22][CH2:21][NH:20][CH2:19][C:18]=4[C:16]=3[CH:17]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68109112tert-butyl 8-(4-methoxyphenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

Product 1

HCID 681089548-(4-Methoxyphenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochlorideYield 30%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To the product of step A (221 mg, 0.50 mmol) in dichloromethane and methanol was added 2 M HCl in diethyl ether (5 mL). After stirring for 18 h, the product was filtered, washed with diethyl ether and lyophilized to give 8-(4-methoxyphenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (50 mg, 30%) as a white solid: mp 270-272° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.64 (s, 2H), 8.35 (d, J=1.5 Hz, 1H), 7.92-7.78 (m, 4H), 7.14-7.09 (m, 2H), 4.38 (s, 2H), 3.82 (s, 3H), 3.52 (t, J=6.0 Hz, 2H), 3.13 (t, J=5.4 Hz, 2H); APCI MS m/z 344 [M+H]+.

Workup

  1. filtrationthe product was filtered
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-bc473ba280404adbb871ba8eb683f015
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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