Water → HCID 59634061, compound

HRID 1615065Notes

Reaction equation

HRID 1615065 reaction equation
[CH2:1]([C:3]1[CH:31]=[CH:30][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:18][N:17]([C:19]([C:21]4[CH:26]=[C:25]([OH:27])[CH:24]=[CH:23][N:22]=4)=[O:20])[CH2:16]3)=[CH:11][C:10]=2[O:28][CH3:29])=[CH:5][CH:4]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:39][CH2:40][OH:41].O>CN(C=O)C>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:18][N:17]([C:19]([C:21]4[CH:26]=[C:25]([O:27][CH2:39][CH2:40][OH:41])[CH:24]=[CH:23][N:22]=4)=[O:20])[CH2:16]3)=[CH:11][C:10]=2[O:28][CH3:29])=[CH:30][CH:31]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 178436440HCID 178436440, compound

Product 1

HCID 59634061HCID 59634061, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of {3-[4-(4-ethylbenzyloxy)-3-methoxyphenyl]azetidin-1-yl}-(4-hydroxypyridin-2-yl)-methanone (9.6 g) prepared in Example 4 (4) and K2CO3 (40 g) in DMF (90 mL) was added 2-bromoethanol (9.6 mL). The reaction mixture was stirred at 80° C. for 11 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over Na2SO4. The solvent was removed under reduced pressure. Diisopropyl ether was added to the residue. The precipitated solid was collected on a filter and dried to give the title compound (8.4 g, 80%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customThe solvent was removed under reduced pressure
  4. additionDiisopropyl ether was added to the residue
  5. customThe precipitated solid was collected on
  6. filtrationa filter
  7. customdried

Sources & evidence

ORD record
ord-c2cbebef646946fb9e2259fd968144a6
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

Loading…