Dimethylformamide → 3-Methylcarboxy-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepine

HRID 84586ノート

反応式

HRID 84586 の反応式
CO[C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[C:7](I)=[N:6][CH:5]=1.CN(C)C=O.[C:25](=O)([O-:27])[O-:26].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:3][C:4]1[C:5]([C:25]([OH:27])=[O:26])=[N:6][C:7]2[C:14]3[S:15][CH:16]=[CH:17][C:13]=3[CH2:12][CH2:11][O:10][C:8]=2[CH:9]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 57900415Methyl 6-iodo-5-(2-(thiophen-3-yl)ethoxy)nicotinate

生成物 1

HCID 668693003-Methylcarboxy-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepine収率 52.8%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 887Methanol溶媒

反応条件

温度
90 °C

実験手順

To a solution of 6-Iodo-5-(2-thiophen-3-yl-ethoxy)-nicotinic acid methyl ester (4.40 g, 11.3 mmol) in N,N-Dimethylformamide (176 mL, 2270 mmol) was added potassium carbonate (9.37 g, 67.8 mmol), triphenylphosphine (1.19 g, 4.52 mmol) and palladium acetate (508 mg, 2.26 mmol). The reaction mixture was stirred at 90° C. 8 h. The reaction mixture was diluted with MeOH then filtered through celite. The filtrate was concentrated. The crude product was purified by flash chromatography EtOAc/Hex (0-100%) (product eluted at 30%) to give 3-methylcarboxy-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepine (52.8%). MS: (ESI+) 262.0

後処理

  1. custom8 h
  2. filtrationthen filtered through celite
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by flash chromatography EtOAc/Hex (0-100%) (product eluted at 30%)

出典と根拠

ORDレコード
ord-ee7a6cabb5254758bbea81f9cabdbe8a
出典データセット
uspto-grants-2014_09
特許番号
US08846762B2

反応ノート

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