Water → Methyl 5-((5,5-dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate

HRID 709802Notes

Reaction equation

HRID 709802 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:19]([OH:20])=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:11]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH:29]1[CH2:33][O:32][C:31]([CH3:35])([CH3:34])[CH2:30]1.O>CN(C=O)C>[CH3:34][C:31]1([CH3:35])[O:32][CH2:33][CH:29]([CH2:28][O:20][C:19]2[C:10]([C:3]3[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=3[F:1])=[N:11][CH:12]=[C:13]([CH:18]=2)[C:14]([O:16][CH3:17])=[O:15])[CH2:30]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 117759971Methyl 6-(2-fluoro-5-methoxyphenyl)-5-hydroxynicotinateHCID 1177602254-(Bromomethyl)-2,2-dimethyloxolane

Product 1

HCID 117760190Methyl 5-((5,5-dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)nicotinateYield 99.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 6-(2-fluoro-5-methoxyphenyl)-5-hydroxynicotinate (700 mg), potassium carbonate (1.10 g) and 4-(bromomethyl)-2,2-dimethyltetrahydrofuran (730 mg) in DMF (5.0 mL) was stirred at 80° C. for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate and the extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (980 mg) as a pale-yellow oil. This compound was used for the next step without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialthe extract was dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cbd6cbcb9b594d9ebcb622ae6cb1cfb6
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

Loading…