Methanol → HCID 22050560, compound

HRID 1867156Notes

Reaction equation

HRID 1867156 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[CH2:14][O:15][C:16]1[CH:21]=[C:20]([CH3:22])[N:19]([C:23]2[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=2[F:30])[C:18](=[O:31])[C:17]=1[Br:32])C.[OH-].[Na+].CO.O>C1COCC1>[Br:32][C:17]1[C:18](=[O:31])[N:19]([C:23]2[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=2[F:30])[C:20]([CH3:22])=[CH:21][C:16]=1[O:15][CH2:14][C:8]1[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:7]=1[O:6][CH2:5][C:4]([OH:33])=[O:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 21035357HCID 21035357, compound

Product 1

HCID 22050560HCID 22050560, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl[2-({[3-bromo-1-(2,6-difluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridin-4-yl]oxy}methyl)-5-fluorophenoxy]acetate (from Step 3) (0.62 g, 1.18 mmol), 1.5 N NaOH solution in 1:1 MeOH:water (1.2 mL, 1.77 mmol), and THF (1.2 mL) were refluxed at 60° C. for 1 h. The solution was concentrated on a rotary evaporator, cooled, and 5% citric acid added. The solid precipitate was filtered and dried in vacuo. Product obtained as a pale yellow solid (0.35 g, 60%). 1H NMR (CD3OD/400 MHz) δ7.59 (m, 1H), 7.49 (m, 1H), 7.22 (m, 2H), 6.75 (m, 2H), 6.72 (s, 1H), 5.43 (s, 2H), 4.66 (s, 2H), 2.07 (s, 3H). ESHRMS m/z 498.0143 and 500.0186 (M+H calculated for C21H16BrF3NO5 requires 498.0158 and 500.0141).

Workup

  1. concentrationThe solution was concentrated on a rotary evaporator
  2. temperaturecooled
  3. addition5% citric acid added
  4. filtrationThe solid precipitate was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-de628b7f89a3455a89e0577c7706d94a
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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