Hydrochloric Acid → 7-[(R)-1-(2,6-dichloro-3-fluorophenyl)-ethoxy]-furo[3,2-c]pyridin-6-ylamine

HRID 911951Notes

Reaction equation

[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@H:10]([O:12][C:13]1[C:14]2[O:24][CH:23]=[CH:22][C:15]=2[CH:16]=[N:17][C:18]=1[N+:19]([O-])=O)[CH3:11].Cl>CCO.[Fe]>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@H:10]([O:12][C:13]1[C:14]2[O:24][CH:23]=[CH:22][C:15]=2[CH:16]=[N:17][C:18]=1[NH2:19])[CH3:11]

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of 7-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridine (40 mg, 0.11 mmol) in EtOH (1 mL) was added Fe powder (24 mg, 0.43 mmol) and 1M HCl (aq.) (0.05 mL, 0.05 mmol). The reaction mixture was stirred at 95° C. for 20 min. After cooled down to room temperature, the reaction mixture was passed through a pad of Celite. The filtrate was concentrated in vacuo and residue was purified by preparative TLC (5% MeOH in DCM) to afford the title compound as a brown oil (25 mg, 68% yield). 1H NMR (CDCl3, 400 MHz): δ=1.86 (d, J=6.60 Hz, 3H), 4.75 (br, s, 2H), 6.55 (q, J=6.97 Hz, 1H), 6.65 (d, J=2.20 Hz, 1H), 7.04 (t, J=8.43 Hz, 1H), 7.27 (dd, J=8.80, 4.77 Hz, 1H), 7.39 (d, J=2.20 Hz, 1H), 8.05 (s, 1H). MS (ES+): m/z 341.03, 343.01 (100) [MH+]. HPLC: tR=2.77 min (ZQ3: polar—5 min).

Workup

temperatureAfter cooled down to room temperature
concentrationThe filtrate was concentrated in vacuo and residue
customwas purified by preparative TLC (5% MeOH in DCM)

Sources & evidence

ORD record: ord-239115e527a64899bae73e40a9c663c8
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022206B2

Reaction notes

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