Potassium Carbonate → (E)-3-[3'-adamantan-1-yl-4'-(2-morpholin-4-yl-ethoxy)biphenyl-4-yl]-acrylic acid methyl ester

HRID 41729

Reaction equation

HRID 41729 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9](=[O:35])/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([C:25]34[CH2:34][CH:29]5[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]5)[CH2:26]3)[CH2:32]4)[CH:19]=2)=[CH:14][CH:13]=1.Cl.Cl[CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>CN(C=O)C>[CH3:7][O:8][C:9](=[O:35])/[CH:10]=[CH:11]/[C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:38][CH2:39][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)=[C:20]([C:25]34[CH2:34][CH:29]5[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]5)[CH2:26]3)[CH2:32]4)[CH:19]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 10293655(E)-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)-acrylic acid methyl ester

Product 1

HCID 67401549(E)-3-[3'-adamantan-1-yl-4'-(2-morpholin-4-yl-ethoxy)biphenyl-4-yl]-acrylic acid methyl esterYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2CO3 (265 mg, 1.92 mmol) was added to a solution of (E)-3-(3′-adamantan-1-yl-4′-hydroxybiphenyl-4-yl)-acrylic acid methyl ester (250 mg, 0.64 mmol) in DMF (2.5 ml) and the mixture was stirred at RT for 30 min. 4-(2-Chloroethyl)-morpholine hydrochloride (155 mg, 0.83 mmol) was added and the solution was heated to 60° C. for 14 h. The reaction was quenched by addition of water and was extracted with EtOAc. The organic layer was washed with a saturated solution of NaHCO3, water and brine, dried over Na2SO4 and evaporated under reduced pressure to obtain (E)-3-[3′-adamantan-1-yl-4′-(2-morpholin-4-yl-ethoxy)biphenyl-4-yl]-acrylic acid methyl ester (193 mg, 60%) after purification on silica gel (EtOAc:hexane 50:50).

Workup

  1. temperaturethe solution was heated to 60° C. for 14 h
  2. customThe reaction was quenched by addition of water
  3. extractionwas extracted with EtOAc
  4. washThe organic layer was washed with a saturated solution of NaHCO3, water and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9fe8e2e7bb804fca82c7cc1036f8b270
Source dataset
uspto-grants-2013_09
Patent number
US08530517B2

Linked notes

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