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

HRID 1916281ノート

反応式

HRID 1916281 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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+].

後処理

  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

出典と根拠

ORDレコード
ord-b1205de7097846d7925c7150108df859
出典データセット
uspto-grants-2013_12
特許番号
US08618121B2

反応ノート

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