Hydrochloric Acid → Ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate

HRID 79491

反応式

HRID 79491 の反応式
Cl/[C:2](/[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3]/[O-].[K+].Cl.O1CCOCC1.[Br:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH2:25])[CH:20]=1>C1(C)C=CC=CC=1>[Br:18][C:19]1[CH:24]=[CH:23][N:22]2[C:2]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][N:25]=[C:21]2[CH:20]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 6932822-Amino-4-bromopyridineHCID 23711836Potassium (E)-2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate

生成物 1

HCID 67260906Ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate収率 74.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Potassium (E)-2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate (4.4 g, 23 mmol; prepared as in Example 65, step B1) was suspended in toluene (40 mL) and a 4M solution of HCl in dioxane (2.0 mL, 8.1 mmol). The mixture was stirred at ambient temperature for 5 minutes. 4-Bromopyridin-2-amine (2.0 g, 12 mmol) was added to the mixture and heated to 40° C. for 22 hours. The mixture was cooled to ambient temperature and extracted with 2M HCl (3×75 mL). Solid K2CO3 was added to the combined aqueous extracts until CO2 evolution ceased. The aqueous phase was extracted with MTBE (2×50 mL), dried over MgSO4, filtered and concentrated to give the product (2.4 g). MS (ES+APCI) m/z=268.7 (M+H).

後処理

  1. temperatureheated to 40° C. for 22 hours
  2. temperatureThe mixture was cooled to ambient temperature
  3. extractionextracted with 2M HCl (3×75 mL)
  4. additionSolid K2CO3 was added to the combined aqueous extracts until CO2 evolution
  5. extractionThe aqueous phase was extracted with MTBE (2×50 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-78e23bd9e68a406c9c5de6f9f892a1c3
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

関連ノート

読み込み中…