Potassium Carbonate → 3-[4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenylamino]-propan-1-ol

HRID 626036Notes

Reaction equation

HRID 626036 reaction equation
[CH2:1]([O:8][C:9]1[CH:23]=[C:22]([CH2:24][CH3:25])[CH:21]=[CH:20][C:10]=1[O:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][C:13]=1[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:33][CH2:34][CH2:35][OH:36]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:23]=[C:22]([CH2:24][CH3:25])[CH:21]=[CH:20][C:10]=1[O:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][CH2:33][CH2:34][CH2:35][OH:36])=[CH:14][C:13]=1[F:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 591912224-(2-Benzyloxy-4-ethylphenoxy)-3-fluoroaniline

Product 1

HCID 591912673-[4-(2-Benzyloxy-4-ethyl-phenoxy)-3-fluoro-phenylamino]-propan-1-olYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[2-(benzyloxy)-4-ethylphenoxy]-3-fluoroaniline (500 mg, 1.48 mmol), K2CO3 (1.23 g, 8.9 mmol) and 3-bromo-1-propanol (410 mg, 2.9 mmol) were taken in dry DMF (2 ml) in a microwave vial and was subjected to microwave at 180° C. for 2 h. The reaction mixture was filtered over celite and the residue washed thoroughly with ethyl acetate. The combined organic fractions including the filtrate were washed with water, brine, dried over Na2SO4 and concentrated. The crude obtained was combined with earlier crude products obtained from a 100 mg and 200 mg batches and purified together by column chromatography over silica gel using 40% ethylacetate in pet ether as eluant to get 400 mg (42.6%) of pure title compound.

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. washthe residue washed thoroughly with ethyl acetate
  3. washwere washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude obtained
  7. customobtained from a 100 mg and 200 mg batches
  8. custompurified together by column chromatography over silica gel using 40% ethylacetate in pet ether as eluant

Sources & evidence

ORD record
ord-fbe6613936da49a081e3d73061b34a9d
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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