1,2,3,4-Tetrahydro-1-naphthalenol → 2-(2,4-Dichlorophenyl)-3,6-diethyl-5-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyrazine

HRID 1612172

반응식

HRID 1612172 반응식
[CH:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[C:15]1[C:20]([CH2:21][CH3:22])=[N:19][C:18]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])=[C:17]([CH2:31][CH3:32])[N:16]=1>CS(C)=O.O>[Cl:30][C:24]1[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=1[C:18]1[C:17]([CH2:31][CH3:32])=[N:16][C:15]([O:11][CH:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)=[C:20]([CH2:21][CH3:22])[N:19]=1

참가 물질

6

반응물 3

HCID 107231,2,3,4-Tetrahydro-1-naphthalenolHCID 24758Sodium hydrideHCID 221474372-Bromo-5-(2,4-dichlorophenyl)-3,6-diethylpyrazine

생성물 1

HCID 101734062-(2,4-Dichlorophenyl)-3,6-diethyl-5-(1,2,3,4-tetrahydronaphthalen-1-yloxy)pyrazine

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매3회HCID 962Water용매

실험 절차

A solution of 1,2,3,4-tetrahydronaphthalen-1-ol (248 mg) in DMSO (3 ml) was added to NaH (100 mg) suspended in DMSO (4 ml). The reaction mixture was stirred at r.t. for 1 hour and heated at 75° C. for 1 hour. 2-bromo-5-(2,4-dichlorophenyl)-3,6-diethylpyrazine in DMSO (3 ml) was added. After 24 h, the rxn mixture was diluted with 30 ml of H2O, extracted with CH2Cl2, washed with NaHCO3, brine, dried (MgSO4), filtered and concentrated. Flash chromatography (1:50 EtOAC:Heptane) gave the title compound: 1H NMR (CDCl3) δ 1.23, 1.95, 2.13, 2.20, 2.58, 2.83, 2.96, 6.46, 7.36; HRMS (ESI+) calcd for C24H24Cl2N2O1 (M+H)+ 427.1344, found 427.1359.

후처리

  1. temperatureheated at 75° C. for 1 hour
  2. waitAfter 24 h
  3. extractionextracted with CH2Cl2
  4. washwashed with NaHCO3, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-739afe6514ee40c3a9bad5001c6fad3b
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06992087B2

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