N-bromobutanimide → 5'-Bromo-1'-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-6'-(4-morpholinyl)-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]

HRID 1618767ノート

反応式

HRID 1618767 の反応式
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:19]3[C:27]4[C:22](=[N:23][CH:24]=[C:25]([N:28]5[CH2:33][CH2:32][O:31][CH2:30][CH2:29]5)[CH:26]=4)[C:21]4([CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH2:20]3)=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[Br:39]N1C(=O)CCC1=O>C(#N)C>[Br:39][C:24]1[N:23]=[C:22]2[C:21]3([CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[CH2:20][N:19]([C:6]3[C:5]4[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=4)[N:9]=[C:8]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=4)[C:7]=3[CH3:18])[C:27]2=[CH:26][C:25]=1[N:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 509390781'-[7-Fluoro-3-Methyl-2-(Pyridin-2-Yl)quinolin-4-Yl]-6'-(Morpholin-4-Yl)-1',2,2',3,5,6-Hexahydrospiro[pyran-4,3'-Pyrrolo[3,2-B]pyridine]

生成物 1

HCID 866642805'-Bromo-1'-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-6'-(4-morpholinyl)-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

To a stirred solution of 1′-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-6′-(4-morpholinyl)-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] (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 (87 mg, 0.489 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 then it was dried over MgSO4, filtered and evaporated in vacuo to give 5′-bromo-1′-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-6′-(4-morpholinyl)-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine]. 1H NMR (400 MHz, chloroform-d) δ ppm 8.74 (1H, dt, J=4.8, 1.4 Hz), 7.83-7.99 (3H, m), 7.70 (1H, dd, J=9.2, 5.9 Hz), 7.42 (1H, ddd, J=6.8, 4.7, 2.2 Hz), 7.28-7.34 (1H, m), 5.97 (1H, s), 4.10-4.20 (2H, m), 3.94-4.06 (2H, m), 3.74-3.84 (4H, m), 3.49-3.64 (2H, m), 2.78-2.94 (4H, m), 2.28-2.46 (5H, m), 1.72-1.88 (2H, m). Mass Spectrum (ESI) m/e=590.0 [(M+1) (79Br)] and 592.0 [(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 materialit was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-6c33958e5192496b9df3cd18c213a45a
出典データセット
uspto-grants-2014_07
特許番号
US08765940B2

反応ノート

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