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

HRID 1824086ノート

反応式

HRID 1824086 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-9db3fc33dade43bc865efc898f37ab52
出典データセット
uspto-grants-2006_05
特許番号
US07041672B2

反応ノート

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