Sulfuric Acid → Methyl 5-bromoisoquinoline-4-carboxylate

HRID 1470482노트

반응식

HRID 1470482 반응식
OS(O)(=O)=O.[CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][N:7]=1.C1C(=O)N([Br:27])C(=O)C1>>[Br:27][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[C:9]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][N:7]=[CH:6]2

참가 물질

4

반응물 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 11830161Methyl Isoquinoline-4-carboxylate

생성물 1

HCID 68281832Methyl 5-bromoisoquinoline-4-carboxylate수율 90.2%

실험 절차

To a mixture of conc. H2SO4 (16 mL) and methyl isoquinoline-4-carboxylate (Intermediate-15) (2.8 g, 15 mmol) at 0° C. was added, NBS (3.3 g, 18.7 mmol) slowly and the reaction mixture was allowed to come to RT and stirred overnight. After completion (TLC), it was quenched with ice, neutralized (NaHCO3) and extracted with EtOAc (50 mL×3). The organic phase was separated, dried (Na2SO4) and concentrated to give dark brown oil (3.6 g) as crude product that was purified by flash column chromatography (25% EtOAc in Hexanes) to furnish the desired compound (1.4 g, 35%).

후처리

  1. additionwas added
  2. customto come to RT
  3. customAfter completion (TLC), it was quenched with ice
  4. extractionextracted with EtOAc (50 mL×3)
  5. customThe organic phase was separated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9f895bbcf45840f2a5ec6561f168bb49
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006442B2

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