Bromine → HCID 18613734、化合物

HRID 705112ノート

反応式

HRID 705112 の反応式
[CH2:1]([C:3]1[N:4]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1)[CH3:2].C([O-])(=O)C.[Na+].[Br:26]Br>C(O)(=O)C>[Br:26][CH:1]([C:3]1[N:4]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1)[CH3:2]

参加物

5

反応物 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 186137392-Ethyl-3-(4-fluorophenyl)pyrido[2,3-d]pyrimidin-4(3H)-one

生成物 1

HCID 18613734HCID 18613734、化合物収率 85.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

反応条件

温度
40 °C

実験手順

A suspension of the quinazolinone (17) (50.0 g, 0.56 mmol) and anhydrous sodium acetate (56 mg) in glacial acetic acid (1.0 mL) was heated to 40° C. and treated dropwise with a solution of bromine (90 mg, 0.56 mmol) in glacial acetic acid (5 mL). Once the starting material was fully consumed by TLC analysis, the mixture was poured onto water (5 mL), basified with saturated aqueous sodium hydrogen carbonate and extracted with tert-butylmethyl ether. The combined organic phases were dried (MgSO4), filtered, and concentrated to a solid which was purified by silica-gel column chromatography [eluent: Ethyl acetate:Hexane, 50:50, ν/ν] to give the title bromide (18) (166 mg. 85%) as an off white solid:

後処理

  1. customOnce the starting material was fully consumed by TLC analysis
  2. additionthe mixture was poured onto water (5 mL)
  3. extractionextracted with tert-butylmethyl ether
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a solid which
  7. customwas purified by silica-gel column chromatography [eluent: Ethyl acetate:Hexane, 50:50, ν/ν]

出典と根拠

ORDレコード
ord-fb77320853704d068e98c6db1898b3b2
出典データセット
uspto-grants-2015_11
特許番号
US09173869B2

反応ノート

読み込み中…