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

HRID 651646노트

반응식

HRID 651646 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dcc1ac5000494091b4319838264fe1af
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06281227B1

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