Acetic Acid → Methyl 5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinate

HRID 405169ノート

反応式

HRID 405169 の反応式
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[F:15][C:16]1[CH:17]=[CH:18][C:19]([CH:32]=O)=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([O:30][CH3:31])=[O:29])=[N:26][CH:27]=2)[CH:21]=1.[Br:34][C:35]1[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][C:36]=1[F:42].CC(O)=O>CCOC(C)=O.ClCCCl>[Br:34][C:35]1[CH:41]=[CH:40][C:38]([NH:39][CH2:32][C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][C:20]=2[C:22]2[CH:23]=[CH:24][C:25]([C:28]([O:30][CH3:31])=[O:29])=[N:26][CH:27]=2)=[CH:37][C:36]=1[F:42]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 8218484-Bromo-3-fluoroanilineHCID 5049666Sodium triacetoxyborohydrideHCID 86674254HCID 86674254、化合物

生成物 1

HCID 71060114Methyl 5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinate

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Solid NaBH(OAc)3 (491 mg, 2.3 mmol) was added to a DCE solution (4 mL) of methyl 5-(5-fluoro-2-formylphenyl)picolinate (300 mg, 1.2 mmol), 4-bromo-3-fluoroaniline (242 mg, 1.3 mmol), and AcOH (0.27 mL, 4.6 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture diluted with EtOAc washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

後処理

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

出典と根拠

ORDレコード
ord-8962f3de38a84cb48e0ff9f948ad15f3
出典データセット
uspto-grants-2014_06
特許番号
US08748624B2

反応ノート

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