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

HRID 2179312Notes

Reaction equation

HRID 2179312 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:23][C:22]4[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][C:17]=4[C:15]=3[CH:16]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[ClH:31]>ClCCl.CO.C(OCC)C>[ClH:31].[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:23][C:22]4[CH2:21][CH2:20][NH:19][CH2:18][C:17]=4[C:15]=3[CH:16]=2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68108458tert-butyl 8-(3-fluorophenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

Product 1

HCID 574143918-(3-Fluorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from step C (135 mg, 0.30 mmol) in dichloromethane (1 mL) and methanol (0.5 mL) was added 2M HCl in diethyl ether (4 mL). After stirring for 14 h at ambient temperature the reaction mixture was diluted with diethyl ether to induce precipitation. The reaction mixture was concentrated in vacuo to give 8-(3-fluorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (96 mg, 96%, AUC HPLC>99%) as an off-white solid: mp 262-272° C. dec; 1H NMR (CD3OD, 300 MHz) δ 8.31-8.27 (m, 1H), 7.97 (dd, J=8.7, 2.1 Hz, 1H), 7.84-7.78 (m, 1H), 7.76-7.69 (m, 2H), 7.64-7.56 (m, 1H), 7.42-7.35 (m, 1H), 4.49 (s, 2H), 3.69 (t, J=6.0 Hz, 2H), 3.23-3.17 (m, 2H); APCI MS m/z 332 [M+H]+.

Workup

  1. customprecipitation
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-81a4c965b71e48b889e9a38d6b9c96d2
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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