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

HRID 2179316Notes

Reaction equation

HRID 2179316 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([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:10])=[O:9])=[CH:4][CH:3]=1.[ClH:24]>CO>[ClH:24].[F:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 681085938-(4-Fluorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine

Product 1

HCID 681089048-(4-Fluorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The product of step B (60 mg, 0.10 mmol) was converted to hydrochloride salt by dissolving in methanol and treating with 1.25 M HCl in methanol. The reaction mixture was concentrated in vacuo to give 8-(4-fluorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (60 mg, 90%, AUC HPLC>99%) as a white solid: mp 270-280° C. <<MP data>>; 1H NMR (CD3OD, 300 MHz) δ 8.27 (d, J=1.8 Hz, 1H), 8.10-8.00 (m, 2H), 7.95 (dd, J=8.7, 2.1 Hz, 1H), 7.71 (d, J=8.7 Hz, 1H), 7.36-7.25 (m, 2H), 4.81 (t, J=1.5 Hz, 2H), 3.69 (t, J=6.0 Hz, 2H), 3.24-3.16 (m, 2H); APCI MS m/z 332 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-b2dd1b656a47482fbbe2892b3fef1123
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

Loading…