Methyl iodide → 3-(4-chlorophenyl)-2-(1-methyl-1H-indol-5-yl)quinazolin-4(3H)-one

HRID 1846375ノート

反応式

HRID 1846375 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11]2[C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][CH:25]=[CH:24]3)=[CH:6][CH:5]=1.[CH3:30]I>C1COCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11]2[C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[N:26]([CH3:30])[CH:25]=[CH:24]3)=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 468423083-(4-chlorophenyl)-2-(1H-indol-5-yl)quinazolin-4(3H)-one

生成物 1

HCID 468403103-(4-chlorophenyl)-2-(1-methyl-1H-indol-5-yl)quinazolin-4(3H)-one収率 65%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

NaH (60% in oil) (0.006 g, 0.14 mmol) was added to a 0° C. solution of 3-(4-chlorophenyl)-2-(1H-indol-5-yl)quinazolin-4(3H)-one (0.14 mmol) in THF (5 mL). After stirring for 15 min, MeI (0.01 mL, 0.16 mmol) was added, and the reaction was warmed to room temperature for 1 hour. After quenching with H2O, diluting with EtOAc, washing with brine, drying with Na2SO4, and filtering, the mixture was concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 10% to 70% EtOAc in heptane, afforded the title compound as a white solid (65%). 1H-NMR (300 MHz, DMSO-d6): δ8.18 (d, J=6.8 Hz, 1H), 7.87-7.90 (m, 1H), 7.75 (d, J=7.8 Hz, 1H), 7.66 (s, 1H), 7.57-7.59 (m, 1H), 7.21-7.47 (m, 6H), 7.12 (d, J=7.0 Hz, 1H), 6.4 (d, J=2.9 Hz, 1H), 3.74 (s, 3H). MS (APCI) m/z: 386 (M+H)+.

後処理

  1. customAfter quenching with H2O
  2. additiondiluting with EtOAc
  3. washwashing with brine
  4. dry with materialdrying with Na2SO4
  5. filtrationfiltering
  6. concentrationthe mixture was concentrated in vacuo
  7. customPurification by flash chromatography on silica gel
  8. washeluting with 10% to 70% EtOAc in heptane

出典と根拠

ORDレコード
ord-853953c7956740749dc2e9602da7cf86
出典データセット
uspto-grants-2015_02
特許番号
US08952021B2

反応ノート

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