Potassium Carbonate → 4-Chloro-3-(2-methyl-5-nitro-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester

HRID 1671521ノート

反応式

HRID 1671521 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH2:18]([O:20][C:21]([C:23]1[C:24]2[S:32][CH:31]=[C:30]([CH2:33]Br)[C:25]=2[C:26]([Cl:29])=[N:27][CH:28]=1)=[O:22])[CH3:19]>C1COCC1.CN(C=O)C.O>[CH2:18]([O:20][C:21]([C:23]1[C:24]2[S:32][CH:31]=[C:30]([CH2:33][O:11][C:3]3[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=3[CH3:1])[C:25]=2[C:26]([Cl:29])=[N:27][CH:28]=1)=[O:22])[CH3:19]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 935762-Methyl-5-nitrophenolHCID 115300973-Bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester

生成物 1

HCID 596673284-Chloro-3-(2-methyl-5-nitro-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

A mixture of 2-methyl-5-nitrophenol (960 mg, 6.07 mmol) (Avocado) and potassium carbonate powder (913 mg, 6.61 mmol) in dry THF (20 mL) and DMF (10 mL) was stirred at 50° C. for 15 minutes before a solution of 3-bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (1.997 g, 5.969 mmol) (from Example 1 supra) in THF (20 mL) was added. The reaction was stirred at 50° C. for 10 hours and the resulting precipitate was collected. The filtrate was concentrated to give more precipitate. The combined solid was stirred in water (30 mL), filtered, washed with water and dried overnight to give 4-chloro-3-(2-methyl-5-nitro-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white solid. (Yield 1.647 g, 68%).

後処理

  1. additionwas added
  2. customthe resulting precipitate was collected
  3. concentrationThe filtrate was concentrated
  4. customto give more precipitate
  5. filtrationfiltered
  6. washwashed with water
  7. customdried overnight

出典と根拠

ORDレコード
ord-7c1a9c15649b419cb2ed386ff533bcbd
出典データセット
uspto-grants-2011_08
特許番号
US07994321B2

反応ノート

読み込み中…