tert-Butanol → 3,3,5-Tribromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

HRID 493144ノート

反応式

HRID 493144 の反応式
[Br:1]Br.[Br:3][C:4]1([Br:14])[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:13].CC(O)(C)C>O>[Br:14][C:4]1([Br:3])[C:12]2[C:7](=[N:8][CH:9]=[C:10]([Br:1])[CH:11]=2)[NH:6][C:5]1=[O:13]

参加物

5

反応物 3

HCID 6386tert-ButanolHCID 24408BromineHCID 138640943,3-Dibromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

生成物 1

HCID 219561923,3,5-Tribromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one収率 85%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
15 °C

実験手順

Bromine (13.4 mL, 0.262 mol) was added dropwise over a period of 30 min to a cooled (ice bath) and stirred suspension of 2 (37.86 g, 0.131 mol) in water:t-BuOH=1:1 (1500 mL). Cooling bath was removed and the mixture was stirred at r.t. overnight. Then the solution was cooled to 15° C. and saturated aqueous solution of NaHCO3 (278 mL) was added. A yellow suspension, which was formed, was concentrated in vacuum (bath temperature <32° C.) until about 1000 mL of condensate was collected. The solid was filtered off, washed with water (200 mL), and dried in vacuum to afford 3 (40.85 g, 85%) as tan powder.

後処理

  1. temperaturea cooled (ice bath)
  2. temperatureCooling bath
  3. customwas removed
  4. stirringthe mixture was stirred at r.t. overnight
  5. additionsaturated aqueous solution of NaHCO3 (278 mL) was added
  6. customA yellow suspension, which was formed
  7. concentrationwas concentrated in vacuum (bath temperature <32° C.) until about 1000 mL of condensate
  8. customwas collected
  9. filtrationThe solid was filtered off
  10. washwashed with water (200 mL)
  11. customdried in vacuum

出典と根拠

ORDレコード
ord-1dcb0246506b4d4ab4d798514a951743
出典データセット
uspto-grants-2009_05
特許番号
US07534800B2

反応ノート

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