Ammonia methanol → HCID 59596673, compound

HRID 2264792Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:21]=[C:20]([C:22]([O:24]CC)=O)[CH:19]=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.CO.[NH3:29]>>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:21]=[C:20]([C:22]([NH2:29])=[O:24])[CH:19]=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 21705897Ammonia methanol

HCID 59596694HCID 59596694, compound

Product 1

HCID 59596673HCID 59596673, compound

Procedure

A solution of ethyl 6-(4-{[(3-fluorophenyl)methyl]oxy}phenyl)-2-pyridinecarboxylate (D3, 110 mg, 0.30 mmol) in MeOH/NH3 (7M, 5 ml) was stirred at 60° C. in a sealed tube for 6 h. The solvent was then evaporated under reduced pressure to afford the title compound (95 mg); MS: (ES/+) m/z: 323 [MH+], C19H15FNO3 requires 322; 1H-NMR (300 MHz, DMSO) δ (ppm): 8.25 (bs, 2H), 8.20 (d, 1H), 8.05 (d, 1H), 7.95 (t, 1H), 7.85 (d, 1H), 7.65 (bs, 1H), 7.40 (t, 1H), 7.30 (d, 2H), 7.15 (t, 1H), 7.10 (d, 2H), 5.20 (s, 2H).

Workup

customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record: ord-9b9a88975dee4795b6683432e9274504
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855218B2

Reaction notes

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