3-Pyridinemethanol → Methyl 1-(4-fluorophenyl)-4-oxo-6-(pyridin-3-ylmethoxy)-1,4-dihydroquinoline-3-carboxylate

HRID 1048880Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[C:11](=[O:19])[C:10]([C:20]([O:22][CH3:23])=[O:21])=[CH:9]2)=[CH:4][CH:3]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30]O)[CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH2:30][C:26]4[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=4)=[CH:15][CH:16]=3)[C:11](=[O:19])[C:10]([C:20]([O:22][CH3:23])=[O:21])=[CH:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Compound L (15 mg, 0.048 mmol, 1.0 eq) and 3-pyridinemethanol (10 mg, 0.096 mmol, 2.0 eq) were dissolved in THF (0.5 mL) and cooled to 0° C. Triphenylphosphine (28 mg, 0.11 mmol, 2.2 eq) and di-tert-butylazodicarboxylate (18 mg, 0.077 mmol, 1.6 eq) were added and the reaction was stirred at room temperature until complete by LCMS. The reaction was concentrated and purified using reverse phase chromatography to afford 15 mg (77%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.69 (d, J=1.7 Hz, 1H), 8.54 (dd, J=4.7, 1.3 Hz, 1H), 8.41 (s, 1H), 7.90-7.88 (m, 1H), 7.79 (d, J=3.0 Hz, 1H), 7.73-7.70 (m, 2H), 7.50 (t, J=8.8 Hz, 2H), 7.43 (dd, J=7.8, 4.8 Hz, 1H), 7.37 (dd, J=9.3, 3.0 Hz, 1H) 6.94 (d, J=9.2 Hz, 1H), 5.28 (s, 2H), 3.72 (s, 3H); ES-MS [M+1]+: 405.2.

Workup

concentrationThe reaction was concentrated
custompurified

Sources & evidence

ORD record: ord-e6665f7d42a04bf3ac2a7f8c40ca3702
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382208B1

Reaction notes

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