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

HRID 1846375노트

반응식

HRID 1846375 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-853953c7956740749dc2e9602da7cf86
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952021B2

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