Potassium Phosphate, Tribasic → 6-Cyclopropyl-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline

HRID 13666

反応式

HRID 13666 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:5]2[N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.[CH:23]1(B(O)O)[CH2:25][CH2:24]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:23]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([CH3:12])[C:6]([S:13]([CH3:16])(=[O:14])=[O:15])=[C:5]3[N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:25][CH2:24]1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 120018106-Bromo-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline2 回

生成物 1

HCID 120018056-Cyclopropyl-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline収率 22.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

6-Bromo-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline (compound of example 6) (0.5 g, 1.3 mmol), cyclopropyboronic acid (0.167 g, 1.95 mmol), potassium phosphate tribasic (0.826 g, 3.89 mmol) and tetrakis(triphenylphosphine)palladium(0) (45 mg, 0.039) were mixed together in dioxane (7 mL) and heated at reflux under argon for 8 h. After extraction with dichloromethane and half-saturated NaCl solution, the crude product was purified chromatography on silica gel in dichloromethane/ethyl acetate with a gradient from 100:0 to 90:10. One obtained 0.1 g (21%) of white crystals. MS: m/z=347 (M+H).

後処理

  1. temperatureheated
  2. temperatureat reflux under argon for 8 h
  3. extractionAfter extraction with dichloromethane and half-saturated NaCl solution
  4. customthe crude product was purified chromatography on silica gel in dichloromethane/ethyl acetate with a gradient from 100:0 to 90:10

出典と根拠

ORDレコード
ord-e3a5e222f59c484bab90c43770ac50bc
出典データセット
uspto-grants-2010_06
特許番号
US07728142B2

関連ノート

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