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

反応式

HRID 1612172 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒3 回HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-739afe6514ee40c3a9bad5001c6fad3b
出典データセット
uspto-grants-2006_01
特許番号
US06992087B2

関連ノート

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