Sodium Bicarbonate → N-(2-amino-5-(pyridin-3-yl)phenyl)pyrrolidine-1-carboxamide

HRID 2201707ノート

反応式

HRID 2201707 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][C:3]=1[NH:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19](B(O)O)[CH:18]=1.C(=O)(O)[O-].[Na+]>C1COCC1.O.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)=[CH:4][C:3]=1[NH:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11]

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 27343783-Pyridinylboronic acidHCID 86712537N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamide

生成物 1

HCID 71466381N-(2-amino-5-(pyridin-3-yl)phenyl)pyrrolidine-1-carboxamide収率 68.9%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
90 °C

実験手順

To a solution of N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamide (0.26 g, 0.72 mmol) in THF (10 mL) and water (5 mL) were added pyridin-3-ylboronic acid (0.13 g, 1.07 mmol, 1.5 equiv.), sodium bicarbonate (0.11 g, 1.07 mmol, 1.5 equiv.) and palladium(0) (0.08 g, 0.07 mmol, 0.1 equiv.). The reaction mass was stirred at 90° C. for sixteen hours. The reaction crude was filtered on a celite bed and diluted in ethyl acetate. The organic layers were washed with water and brine then dried over Na2SO4 and concentrated. The residue was purified by column chromatography on eluting ethyl acetate and hexane to allow N-(2-amino-5-(pyridin-3-yl)phenyl)pyrrolidine-1-carboxamide (0.14 g, 63% yield).

後処理

  1. customThe reaction crude
  2. filtrationwas filtered on a celite bed
  3. additiondiluted in ethyl acetate
  4. washThe organic layers were washed with water and brine
  5. dry with materialthen dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography
  8. washon eluting ethyl acetate and hexane

出典と根拠

ORDレコード
ord-2f7fc84e83604e9897f456091a5c05e2
出典データセット
uspto-grants-2016_06
特許番号
US09365498B2

反応ノート

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