Cesium carbonate → Ethyl 2-methyl-2-{2-methyl-4-[([4-(trifluoromethyl)benzyl]{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]phenoxy}propanoate

HRID 1269585노트

반응식

HRID 1269585 반응식
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[CH:12][C:11]=1[CH3:29])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]2[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=2)[N:32]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:8][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]([F:27])([F:28])[F:26])=[CH:23][CH:24]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:44])([F:46])[F:45])=[CH:39][CH:38]=3)[N:32]=2)=[CH:12][C:11]=1[CH3:29])([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 184483252-Bromo-6-(4-(trifluoromethyl)phenyl)pyridineHCID 18448415Ethyl 2-methyl-2-[2-methyl-4-({[4-(trifluoromethyl) benzyl]amino}methyl)phenoxy]propanoate

생성물 1

HCID 18448414Ethyl 2-methyl-2-{2-methyl-4-[([4-(trifluoromethyl)benzyl]{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]phenoxy}propanoate수율 45.7%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

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온도
70 °C

실험 절차

A mixture of ethyl 2-methyl-2-[2-methyl-4-({[4-(trifluoromethyl)benzyl]amino}methyl)phenoxy]propanoate (0.13 g, 0.318 mmol ), 2-bromo-6-[4-(trifluoromethyl) phenyl]pyridine (78.5 mg, 0.26 mmol), palladium (II) acetate (4.8 mg, 0.021 mmol), (R)-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (19.8 mg, 0.032 mmol) and caesium carbonate (0.13 g, 0.397 mmol) in toluene (1.8 mL) were heated at 70° C. in a reactivial for 18 hours. After cooling to room temperature, the reaction mixture was filtered and the solvent removed in vacuo. Purification by SPE (Silica, 10 g) eluting with 99:1–19:1 cyclohexane:EtOAc afforded the title compound as a colourless oil (75 mg).

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered
  3. customthe solvent removed in vacuo
  4. customPurification by SPE (Silica, 10 g)
  5. washeluting with 99:1–19:1 cyclohexane

출처 및 근거

ORD 기록
ord-d4bec3a271f24532b82a51b03dcfcd1f
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199239B2

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