Acetamide → Methyl 5-acetamido-6-(2,2,2-trifluoroethoxy)nicotinate

HRID 623450ノート

反応式

HRID 623450 の反応式
Cl[C:2]1[C:3]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:18]([NH2:21])(=[O:20])[CH3:19].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>C(O)(C)(C)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.O>[C:18]([NH:21][C:2]1[C:3]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])(=[O:20])[CH3:19]

参加物

9

反応物 4

HCID 178AcetamideHCID 62657Potassium Phosphate, TribasicHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 67509641HCID 67509641、化合物

生成物 1

HCID 67510072Methyl 5-acetamido-6-(2,2,2-trifluoroethoxy)nicotinate収率 18%

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

A mixture of methyl 5-chloro-6-(2,2,2-trifluoroethoxy)nicotinate (3.08 g, 11.4 mmol, Step-1), acetamide (0.70 mL, 13.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.73 g, 0.80 mmol), potassium phosphate (7.27 g, 34.3 mmol) and 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (0.34 g, 0.800 mmol) in tert-butyl alcohol (114 mL) is stirred for 3 hours at 110° C. The reaction mixture is poured into water and extricated with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (3:1 to 1:1) to give 0.59 g (18% yield) of the title compound as a white solid.

後処理

  1. dry with materialdried over sodium sulfate
  2. concentrationconcentrated in vacuo
  3. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (3:1 to 1:1)

出典と根拠

ORDレコード
ord-a0285588f61546bb85b83ffe530def13
出典データセット
uspto-grants-2016_04
特許番号
US09302991B2

反応ノート

読み込み中…