Methanol → HCID 86690763, compound

HRID 1471721Notes

Reaction equation

HRID 1471721 reaction equation
O1CC[O:3][CH:2]1[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[N:9]=[CH:8][C:7]=1[O:14][CH2:15][C:16]1[C:17]([C:22]([OH:24])=[O:23])=[N:18][CH:19]=[CH:20][CH:21]=1.O=S(Cl)Cl.[CH3:29]O>>[CH:2]([C:6]1[CH:11]=[C:10]([O:12][CH3:13])[N:9]=[CH:8][C:7]=1[O:14][CH2:15][C:16]1[C:17]([C:22]([O:24][CH3:29])=[O:23])=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 86690764HCID 86690764, compound

Product 1

HCID 86690763HCID 86690763, compound

Procedure

To 3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)picolinic acid (55 mg, 0.17 mmol, 1 equiv) in MeOH (15 mL) was added SOCl2 (5.0 mL). The mixture was heated to reflux O/N, concentrated, and neutralized to pH 8-9 with NaHCO3(sat.) solution. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give methyl 3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)picolinate (51.5 mg, quantitative yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.44 (s, 1H), 8.67 (dd, J=4.6, 1.5 Hz, 1H), 8.14 (dd, J=8.0, 1.5 Hz, 1H), 8.03 (s, 1H), 7.51 (dd, J=8.0, 4.6 Hz, 1H), 7.06 (s, 1H), 5.60 (s, 2H), 3.95 (s, 3H), 3.85 (s, 3H). LRMS (M+H+) m/z 303.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux O/N
  3. concentrationconcentrated
  4. extractionThe aqueous layer was extracted with EtOAc three times
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified on silica gel using
  8. additiona mixture of EtOAc and hexanes as eluent

Sources & evidence

ORD record
ord-96a6bfede0334feba99b108799a15f82
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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