N,N,N',N'-Tetramethylethylenediamine → 1-Benzenesulfonyl-4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 651646ノート

反応式

HRID 651646 の反応式
C([N-]C(C)C)(C)C.[Li+].CN(C)CCN(C)C.[C:17]1([S:23]([N:26]2[C:34]3[CH:33]=[CH:32][N:31]=[C:30]([Cl:35])[C:29]=3[CH:28]=[CH:27]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl[C:37]([O:39][CH2:40][CH3:41])=[O:38]>C1COCC1>[CH2:40]([O:39][C:37]([C:27]1[N:26]([S:23]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)(=[O:25])=[O:24])[C:34]2[CH:33]=[CH:32][N:31]=[C:30]([Cl:35])[C:29]=2[CH:28]=1)=[O:38])[CH3:41]

参加物

6

反応物 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 10928Ethyl chloroformateHCID 2724682Lithium diisopropylamideHCID 181764061-(Phenylsulfonyl)-4-chloro-5-azaindole

生成物 1

HCID 538353831-Benzenesulfonyl-4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester収率 117%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Lithium diisopropylamide (3.2 mL of a 1.5 M solution in THF, 4.80 mmol) is added to a solution of tetramethylethylenediamine (0.71 mL, 4.75 mmol) and 1-benzenesulfonyl-4-chloro-1H -pyrrolo[3,2-c]pyridine (1 g, 3.42 mmol) in THF (13 mL). The resulting yellow solution is stirred at −78° C. for 1 hour, and then ethyl chloroformate (0.78 mL, 8.16 mmol) is added dropwise. The mixture is slowly brought to room temperature over a 3.5 hour period. The reaction is quenched with saturated NH4Cl solution and then diluted with ethyl acetate. The organic layer is washed with brine, dried over MgSO4, filtered and concentrated to give a light brown solid (1.46 g) as the product which is used in the subsequent step without further purification.

後処理

  1. waitThe mixture is slowly brought to room temperature over a 3.5 hour period
  2. customThe reaction is quenched with saturated NH4Cl solution
  3. additiondiluted with ethyl acetate
  4. washThe organic layer is washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-dcc1ac5000494091b4319838264fe1af
出典データセット
uspto-grants-2001_08
特許番号
US06281227B1

反応ノート

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