2-(Tributylstannyl)pyrazine → [3-Methyl-6-pyrazin-2-yl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1517115

反応式

HRID 1517115 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])[C:5]([CH3:21])=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1.C([Sn](CCCC)(CCCC)[C:37]1[CH:42]=[N:41][CH:40]=[CH:39][N:38]=1)CCC>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:21][C:5]1[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])=[N:7][C:2]([C:37]2[CH:42]=[N:41][CH:40]=[CH:39][N:38]=2)=[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH:4]=1

参加物

5

反応物 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 44547211[6-Chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

生成物 1

HCID 44547647[3-Methyl-6-pyrazin-2-yl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone収率 50.5%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

To a degassed solution of 0.20 g (0.44 mmol) of [6-chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 3) in 8.0 ml of DMF was added 0.051 g (0.044 mmol) of tetrakis-(triphenylphosphine)-palladium and the reaction mixture was stirred for 20 min at RT. Then, 0.49 g (1.32 mmol) of 2-tributylstannanyl-pyrazine were added and the reaction was heated up to 100° C. After 6 hours, it was cooled down to RT, poured into crashed ice and extracted three times with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1) to give 0.11 g (50%) of the title compound as yellow oil. MS: 496.2 (MH−).

後処理

  1. temperaturethe reaction was heated up to 100° C
  2. waitAfter 6 hours
  3. temperatureit was cooled down to RT
  4. additionpoured
  5. extractionextracted three times with EtOAc
  6. washthe organic phases were washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1)

出典と根拠

ORDレコード
ord-f92cfb1354e34de6ace0f3171e2e4ade
出典データセット
uspto-grants-2012_07
特許番号
US08227613B2

関連ノート

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