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N-bromobutanimide → 4-(5-bromo-3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline

HRID 1618770
ノート
印刷プレビュー

反応式

HRID 1618770 の反応式
[CH3:1][C:2]1([CH3:35])[C:6]2=[N:7][CH:8]=[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH:10]=[C:5]2[N:4]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([F:27])=[CH:24][CH:25]=3)[N:20]=[C:19]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[C:18]=2[CH3:34])[CH2:3]1.C1C(=O)N([Br:43])C(=O)C1>C(#N)C>[Br:43][C:8]1[N:7]=[C:6]2[C:2]([CH3:35])([CH3:1])[CH2:3][N:4]([C:17]3[C:26]4[C:21](=[CH:22][C:23]([F:27])=[CH:24][CH:25]=4)[N:20]=[C:19]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[C:18]=3[CH3:34])[C:5]2=[CH:10][C:9]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 509393384-(3,3-Dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline

生成物 1

HCID 866642814-(5-bromo-3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

To a stirred solution of 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline (250 mg, 0.489 mmol) in acetonitrile (6 mL) at 0° C. was added dropwise via syringe over 5 min a solution of n-bromosuccinimide (76 mg, 0.426 mmol) in acetonitrile (4 mL). The reaction was stirred at this temperature for 15 min. After this time the reaction was partitioned between EtOAc (40 mL) and water (15 mL). The separated organic layer was washed with NaHCO3 (15 mL, saturated aqueous solution) and Na2S2O3 (15 mL, saturated aqueous solution) and dried over MgSO4, filtered and evaporated in vacuo to give 4-(5-bromo-3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline. 1H NMR (400 MHz, chloroform-d) δ ppm 8.64-8.82 (1H, m), 7.85-7.97 (3H, m), 7.75 (1H, dd, J=9.2, 5.9 Hz), 7.40-7.45 (1H, m), 7.31 (1H, ddd, J=9.3, 8.0, 2.6 Hz), 5.97 (1H, s), 3.71-3.90 (6H, m), 2.77-2.94 (4H, m), 2.38 (3H, s), 1.58 (3H, s), 1.52 (3H, s). Mass Spectrum (ESI) m/e=548.0 [(M+1) (79Br)] and 550.0 [(M+1) (81Br)]

後処理

  1. customAfter this time the reaction was partitioned between EtOAc (40 mL) and water (15 mL)
  2. washThe separated organic layer was washed with NaHCO3 (15 mL, saturated aqueous solution) and Na2S2O3 (15 mL, saturated aqueous solution)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-f825b2078bb9472e962cec21cd62b82d
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08765940B2

反応ノート

読み込み中…

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