Phosphorus oxychloride → 4-chloro-9H-pyrimido(4,5-b)indole

HRID 1916281노트

반응식

HRID 1916281 반응식
[N:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[C:4](=O)[NH:3][CH:2]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:4]1[C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:1]=[CH:2][N:3]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 1354360363H,4H,9H-pyrimido[4,5-b]indol-4-one

생성물 1

HCID 58064084-chloro-9H-pyrimido(4,5-b)indole

실험 절차

A suspension of 3H-pyrimido[4,5-b]indol-4(9H)-one (0.091 g, 0.491 mmol) in phosphorous oxychloride (8 mL) was refluxed under nitrogen for 24 hours. Phosphorous oxychloride was removed by evaporation and the residue was partitioned between water (20 mL) and chloroform (2×20 mL). The organic extracts were filtered through celite, dried (Na2SO4) and concentrated to give 4-chloro-9H-pyrimido[4,5-b]indole as a yellow solid (0.103 g, 0.50 mmol, quantitative). 1H NMR (500 MHz, CDCl3) δ 7.60 (1H, dd, J=8.8 Hz), 7.70 (1H, dd, J=8.8 Hz), 8.43 (1H, d, J=8 Hz), 8.52 (1H, d, J=8 Hz), 8.98 (1H, s); LC-MS (3) Rt: 5.59 min; m/z (ESI) 206, 204 [MH+].

후처리

  1. temperaturewas refluxed under nitrogen for 24 hours
  2. customPhosphorous oxychloride was removed by evaporation
  3. customthe residue was partitioned between water (20 mL) and chloroform (2×20 mL)
  4. filtrationThe organic extracts were filtered through celite
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b1205de7097846d7925c7150108df859
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618121B2

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