Phenol → HCID 89781951、化合物

HRID 1056066ノート

反応式

HRID 1056066 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[N:8]=[CH:7]2.C(=O)([O-])[O-].[Cs+].[Cs+].[C:19]1([OH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[N:8]=[CH:7]2

参加物

5

反応物 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 457900618-Bromo-2-chloroquinazoline

生成物 1

HCID 89781951HCID 89781951、化合物収率 71.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

A mixture of 8-bromo-2-chloroquinazoline (Ark Pharm Inc, Libertyville Ill.; 0.550 g, 2.259 mmol), cesium carbonate (0.883 g, 2.71 mmol), and phenol (0.234 g, 2.485 mmol) in 3 mL DMSO was sealed and heated to 120° C. for 2 h. The reaction was then partitioned between water and EtOAc. The organic layer was sequentially washed with water (2×), and saturated aq. NaCl (1×), then dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The material was treated with DCM and purified by silica gel chromatography using 0-20% EtOAc/hexane. The material-containing fractions were concentrated to afford 8-bromo-2-phenoxyquinazoline (0.486 g, 1.614 mmol, 71% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 9.25 (1H, s), 8.15 (1H, dd, J=7.6, 1.4 Hz), 7.87 (1H, dd, J=8.0, 1.4 Hz), 7.34-7.50 (5H, m), 7.26-7.31 (1H, m). m/z (ESI, +ve) 302.9 (M+H)+.

後処理

  1. customwas sealed
  2. customThe reaction was then partitioned between water and EtOAc
  3. washThe organic layer was sequentially washed with water (2×), and saturated aq. NaCl (1×)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThe material was treated with DCM
  8. custompurified by silica gel chromatography
  9. concentrationThe material-containing fractions were concentrated

出典と根拠

ORDレコード
ord-41d80927b23c4b1e95f077c02fd22222
出典データセット
uspto-grants-2016_07
特許番号
US09394297B2

反応ノート

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