4-(hydroxymethyl)-5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)pyridin-3-ol → 3-hydroxy-5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)isonicotinaldehyde

HRID 1471734Notes

Reaction equation

[OH:1][CH2:2][C:3]1[C:8]([O:9][CH2:10][C:11]2[C:12]([C:17]3[N:21]([CH:22]([CH3:24])[CH3:23])[N:20]=[CH:19][CH:18]=3)=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][N:6]=[CH:5][C:4]=1[OH:25]>CC#N.O=[Mn]=O>[OH:25][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([O:9][CH2:10][C:11]2[C:12]([C:17]3[N:21]([CH:22]([CH3:24])[CH3:23])[N:20]=[CH:19][CH:18]=3)=[N:13][CH:14]=[CH:15][CH:16]=2)[C:3]=1[CH:2]=[O:1]

Participants

Conditions

Temperature: 46 °C

Procedure

To 4-(hydroxymethyl)-5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)pyridin-3-ol (26 mg, 0.076 mmol, 1 eq.) in CH3CN (10 mL) was added MnO2 (66 mg, 0.76 mmol, 10 eq.). The mixture was heated to 46° C. with stirring O/N, cooled to rt, filtered, and concentrated to give 3-hydroxy-5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)isonicotinaldehyde as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 11.06 (s, 1H), 10.35 (s, 1H), 8.70 (dd, J=4.7, 1.5 Hz, 1H), 8.11 (s, 1H), 7.89 (dd, J=7.9, 1.1 Hz, 1H), 7.80 (s, 1H), 7.53 (d, J=1.8 Hz, 1H), 7.36 (dd, J=7.9, 4.8 Hz, 1H), 6.27 (d, J=1.8 Hz, 1H), 5.14 (s, 2H), 4.61 (sep, J=6.6 Hz, 1H), 1.41 (d, 1=6.6 Hz, 6H). LRMS (M+H+) m/z 339.1

Workup

temperaturecooled to rt
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-dcbc03a2e47e489185e4039b7223c38c
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012450B2

Reaction notes

Loading…