Pyridine → HCID 59128704、化合物

HRID 1991118ノート

反応式

HRID 1991118 の反応式
[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

参加物

6

反応物 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chloride2 回HCID 591286662-(3-bromo-1H-pyrrolo[2,3-b]pyridin-5-yl)isoindoline-1,3-dione

生成物 1

HCID 59128704HCID 59128704、化合物収率 35%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b08a24cb45da420c8339ef8b0dcb8459
出典データセット
uspto-grants-2010_01
特許番号
US07645769B2

反応ノート

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