Diisopropylamine → 2-[4-(5-methylisoxazol-4-yl)phenyl]-N-[(1R)-1-(5-vinylpyridin-2-yl)ethyl]acetamide

HRID 254693

反応式

HRID 254693 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:25])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[N:21][O:22][C:23]=3[CH3:24])=[CH:15][CH:14]=2)[CH3:9])=[N:6][CH:7]=1.[CH:26](B1OC(C)(C)C(C)(C)O1)=[CH2:27].CC1C(P(C2C(C)=CC(C)=C(S([O-])(=O)=O)C=2)C2C(C)=CC(C)=C(S([O-])(=O)=O)C=2)=CC(S([O-])(=O)=O)=C(C)C=1.[Na+].[Na+].[Na+].C(NC(C)C)(C)C>CC#N.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:24][C:23]1[O:22][N:21]=[CH:20][C:19]=1[C:16]1[CH:17]=[CH:18][C:13]([CH2:12][C:11]([NH:10][C@@H:8]([C:5]2[CH:4]=[CH:3][C:2]([CH:26]=[CH2:27])=[CH:7][N:6]=2)[CH3:9])=[O:25])=[CH:14][CH:15]=1

参加物

8

反応物 4

HCID 7912DiisopropylamineHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 11239198TxptsHCID 24765670N-[(1R)-1-(5-bromopyridin-2-yl)ethyl]-2-[4-(5-methylisoxazol-4-yl)phenyl]acetamide

生成物 1

HCID 247655772-[4-(5-methylisoxazol-4-yl)phenyl]-N-[(1R)-1-(5-vinylpyridin-2-yl)ethyl]acetamide

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of 0.18 g (0.46 mmol) N-[(1R)-1-(5-bromopyridin-2-yl)ethyl]-2-[4-(5-methylisoxazol-4-yl)phenyl]acetamide in 0.50 ml CH3CN and 0.50 ml water was added 0.07 g (0.46 mmol) 2-vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.02 g (0.03 mmol) TXPTS, 0.003 g (0.01 mmol) Palladium (II) acetate, and 0.13 mL (0.92 mmol) diisopropylamine. After 20 min in the microwave at 120° C., the reaction mixture was cooled, extracted with CH2Cl2, and washed with brine. The organic layer was dried over NaSO4, filtered, and concentrated in vacuo. Purification by flash chromatography (1×14 cm silica gel, linear gradient 40-85% EtOAc:hexane) afforded 2-[4-(5-methylisoxazol-4-yl)phenyl]-N-[(1R)-1-(5-vinylpyridin-2-yl)ethyl]acetamide. Electrospray mass spec M+H=348.1.

後処理

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over NaSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (1×14 cm silica gel, linear gradient 40-85% EtOAc:hexane)

出典と根拠

ORDレコード
ord-9e45eab71622477bab1167d7322fd753
出典データセット
uspto-grants-2011_01
特許番号
US07875636B2

関連ノート

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