Triethylamine → 7-[(6-Chloro-pyridine-3-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 1986648ノート

反応式

HRID 1986648 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:18][O:19][C:20]([C:22]1[S:26][C:25]2[C:27]([NH2:31])=[CH:28][CH:29]=[CH:30][C:24]=2[CH:23]=1)=[O:21]>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCOC(C)=O>[CH3:18][O:19][C:20]([C:22]1[S:26][C:25]2[C:27]([NH:31][C:6]([C:5]3[CH:4]=[N:3][C:2]([Cl:1])=[CH:10][CH:9]=3)=[O:8])=[CH:28][CH:29]=[CH:30][C:24]=2[CH:23]=1)=[O:21]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 792226-Chloronicotinic acidHCID 45089769Methyl 7-amino-1-benzothiophene-2-carboxylate

生成物 1

HCID 577224537-[(6-Chloro-pyridine-3-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester収率 68%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 6-chloronicotinic acid (1.5 eq) and triethylamine (2.0 eq) in CH2Cl2 (5 mL) was added BopCl (2.0 eq). After 15 min, 7-amino-benzo[b]thiophene-2-carboxylic acid methyl ester (87 mg) in CH2Cl2 and 4-dimethylaminopyridine (DMAP) (1.0 eq) were added to the reaction solution above. The reaction was stirred at room temperature 12 h. The reaction was then diluted with EtOAc, and washed with NaHCO3 solution and brine. The organics were dried over MgSO4, filtered and concentrated to give a crude material which was purified by flash chromatography on silica gel (20%-50% EtOAc/hexane) to provide 100 mg (68%) of the desired 7-[(6-chloro-pyridine-3-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester as a light yellow solid.

後処理

  1. washwashed with NaHCO3 solution and brine
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude material which
  6. customwas purified by flash chromatography on silica gel (20%-50% EtOAc/hexane)

出典と根拠

ORDレコード
ord-97913e13830a40e3b398e9413a0d80c9
出典データセット
uspto-grants-2009_06
特許番号
US07550461B2

反応ノート

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