Pyridine → HCID 59128704, 화합물

HRID 1991118노트

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HRID 1991118 반응식
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([N:21]3[C:29](=[O:30])[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:22]3=[O:31])[CH:19]=2)[NH:14][CH:13]=1.N1C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([N:21]3[C:22](=[O:31])[C:23]4[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:29]3=[O:30])[CH:19]=2)[N:14]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:13]=1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chloride2회HCID 591286662-(3-bromo-1H-pyrrolo[2,3-b]pyridin-5-yl)isoindoline-1,3-dione

생성물 1

HCID 59128704HCID 59128704, 화합물수율 35%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

PhSO2Cl (24 mg, 0.136 mmol) was added dropwise over a period of 3 min. to a stirred solution of 42 (31 mg, 0.090 mmol) and pyridine (11.4 mg, 0.144 mmol) in CH2Cl2. The mixture was stirred at r.t. overnight. Additional portion of PhSO2Cl (24 mg, 0.136 mmol) was added, followed by DMAP (3 mg, 0.025 mmol). After additional stirring for 1.5 h, the mixture was partitioned between saturated aqueous NaHCO3:CH2Cl2. The aqueous layer was extracted with CH2Cl2. The combined organic solutions were washed with brine, dried (MgSO4) and concentrated. Purification by PTLC using AcOEt:hexane=1:1 (v/v) as eluent afforded 43 as orange powder (15 mg, 35%). 1H NMR (400 MHz; CDCl3) δ 7.55 (tt, J=6.6, 1.6 Hz, 2H), 7.62 (tt, J=5.3, 2.0 Hz, 1H), 7.84 (dd, J=5.4, 3.0 Hz, 2H), 7.88 (s, 1H), 7.92 (d, J=2.3 Hz, 1H), 7.98 (dd, J=5.4, 3.0 Hz, 2H), 8.23 (dd, J=4.0, 1.3 Hz, 2H), 8.55 (d, J=1.9 Hz, 1H).

후처리

  1. stirringAfter additional stirring for 1.5 h
  2. customthe mixture was partitioned between saturated aqueous NaHCO3
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic solutions were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by PTLC

출처 및 근거

ORD 기록
ord-b08a24cb45da420c8339ef8b0dcb8459
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645769B2

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