Hydrochloric Acid → [2-Bromo-5-(4-chlorophenyl)pyridin-3-yl]methylamine

HRID 734870ノート

反応式

HRID 734870 の反応式
C=O.[C:3]([BH3-])#[N:4].[Na+].[Br:7][C:8]1[C:13](N)=[CH:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:10][N:9]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.CC(O)=O>[Br:7][C:8]1[C:13]([CH2:3][NH2:4])=[CH:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:10][N:9]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 859697042-Bromo-5-(4-chloro-phenyl)-pyridin-3-ylamine

生成物 1

HCID 86601137[2-Bromo-5-(4-chlorophenyl)pyridin-3-yl]methylamine

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6342Acetonitrile溶媒

実験手順

1.32 mL (17.63 mmol) of formalin solution (37% in water) and 443 mg (7.05 mmol) of sodium cyanoborohydride were added to a solution of 0.50 g (1.76 mmol) of 2-bromo-5-(4-chlorophenyl)pyridin-3-ylamine (Example 16.1c) in 20 mL of acetonitrile, the mixture was acidified to pH 4 with HOAc, and stirred for 16 hours at RT. The reaction mixture was acidified with 4M aqueous HCl and stirred for 1 hour at RT. It was made alkaline with sat. aqueous sodium carbonate solution and the aqueous phase was exhaustively extracted with DCM. The combined organic phases were dried over magnesium sulfate and evaporated down in vacuo. The residue was purified by chromatography (silica gel, gradient PE/DCM 50:50→100:0). Yield: 0.24 g (46% of theoretical); C12H10BrClN2 (M=297.578); calc.: molpeak (M+H)+: 297/299/301 (BrCl); found: molpeak (M+H)+:297/299/301 (BrCl); HPLC-MS: 6.09 minutes (method B).

後処理

  1. stirringstirred for 1 hour at RT
  2. extractionthe aqueous phase was exhaustively extracted with DCM
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customevaporated down in vacuo
  5. customThe residue was purified by chromatography (silica gel, gradient PE/DCM 50:50→100:0)
  6. custom6.09 minutes (method B)

出典と根拠

ORDレコード
ord-9c9580a458284edb993b0882e5151c77
出典データセット
uspto-grants-2009_09
特許番号
US07592358B2

反応ノート

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