Hydrochloric Acid → 6-bromo-1-(1-methylethyl)-1H-indole-4-carboxylic acid

HRID 62401노트

반응식

HRID 62401 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:14]([O:16]C)=[O:15])[C:5]2[CH:6]=[CH:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[OH-].[Na+].Cl>CO.O1CCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=[O:15])[C:5]2[CH:6]=[CH:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2회HCID 67466539methyl 6-bromo-1-isopropyl-1H-indole-4-carboxylate

생성물 1

HCID 674686386-bromo-1-(1-methylethyl)-1H-indole-4-carboxylic acid수율 99%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 6-bromo-1-(1-methylethyl)-1H-indole-4-carboxylate (0.52 g, 1.756 mmol) in methanol (15 mL) and tetrahydrofuran (3 mL) was added 3 M NaOH (1.756 mL, 5.27 mmol) via syringe drop wise (over 2 min). The solution was maintained at RT for 2 h, at which time LCMS showed only 12% conversion to product. Then 1.5 mL 3 M NaOH was added and the solution was maintained at RT overnight. LCMS showed complete conversion to product. Removed volatiles in vacuo and dissolved the residue in water and slowly acidified with 1 M HCl (solids precipitated). Extracted with EtOAc (2×), combined organics and dried over MgSO4. Filtered and concentrated in vacuo to give 6-bromo-1-(1-methylethyl)-1H-indole-4-carboxylic acid (0.50 g, 1.737 mmol, 99% yield) as a white solid.

후처리

  1. temperaturethe solution was maintained at RT overnight
  2. extractionExtracted with EtOAc (2×)
  3. dry with materialdried over MgSO4
  4. filtrationFiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7c467e347d8f4e17bb03d841347ec3a2
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446041B2

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