2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 67195229, 화합물

HRID 1853261노트

반응식

HRID 1853261 반응식
COC(C1N=CC2C(C=1)=CC(OC)=C(OC)C=2)=O.[CH3:19][O:20][C:21]([CH:23]1[CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][C:30]=2[Br:33])[CH2:25][NH:24]1)=[O:22].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCCC1>[Br:33][C:30]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:31]=1[CH:32]=[C:23]([C:21]([O:20][CH3:19])=[O:22])[N:24]=[CH:25]2

참가 물질

5

반응물 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 11096910HCID 11096910, 화합물HCID 44890925Methyl 5-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

생성물 1

HCID 67195229HCID 67195229, 화합물수율 91.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

methyl-5-bromo-isoquinoline-3-carboxylate was prepared using the following procedure describe in US054777252 for methyl-6,7-dimethoxy-isoquinoline-3-carboxylate: 5-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester (880 mg, 3.26 mmol) was treated with 2,3-Dichloro-5,6-dicyanobenzoquinone (1.62 mg, 7.19 mmol) in dry tetrahydrofuran (19 ml) at reflux temperature for 18 hours. The cooled dark mixture was filtered and the solid washed with dichloromethane. The filtrate was treated with a 1M aqueous sodium hydroxide solution and the aqueous layer was extracted twice with dichloromethane. The organic layer was washed with water, brine, dried over sodium sulfate and concentrated to dryness. The residue was purified by flash chromatography over silica gel (gradient cyclohexane/ethyl acetate: 0-100%) to yield methyl 5-bromo-isoquinoline-3-carboxylate (793 mg, 91%) as beige solid.

후처리

  1. custommethyl-5-bromo-isoquinoline-3-carboxylate was prepared
  2. temperatureat reflux temperature for 18 hours
  3. filtrationThe cooled dark mixture was filtered
  4. washthe solid washed with dichloromethane
  5. additionThe filtrate was treated with a 1M aqueous sodium hydroxide solution
  6. extractionthe aqueous layer was extracted twice with dichloromethane
  7. washThe organic layer was washed with water, brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated to dryness
  10. customThe residue was purified by flash chromatography over silica gel (gradient cyclohexane/ethyl acetate: 0-100%)

출처 및 근거

ORD 기록
ord-763072794b574f3fb996cf382cfe8ce2
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962627B2

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