Tetrahydrofuran → 7-Benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

HRID 1481182노트

반응식

HRID 1481182 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[O:15]CC1C=CC=CC=1)=[CH:12][CH:11]=[C:10](Br)[CH:9]=2)=[O:4].C1COCC1.[Br-].[CH2:30]([Zn+])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[NH4+].[Cl-]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:9]=2)=[O:4]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 89812966Methyl 4-(benzyloxy)-7-bromoisoquinoline-3-carboxylateHCID 178419772HCID 178419772, 화합물

생성물 1

HCID 671101307-Benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester수율 16.2%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

To a mixture of 4-benzyloxy-7-bromo-isoquinoline-3-carboxylic acid methyl ester (150 mg, 0.40 mmol), Pd(PPh3)4 (47 mg, 0.040 mmol) and THF (4 mL) was added benzylzinc bromide (2 mL, 1.0 mmol, 0.5 M in THF), and the resulting mixture was refluxed for 16 h under nitrogen atmosphere. After cooling the mixture to r.t., saturated NH4Cl (50 mL) and CH2Cl2 (50 mL) were added. The aqueous layer was extracted with additional CH2Cl2, and the organic layers were combined and dried over MgSO4. After evaporating the solvent, the crude product was purified by column chromatography (0-35% EtOAc/hexanes) to give 19 mg of the title compound as a yellow solid. MS: (+) m/z 294.05 (M+1).

후처리

  1. temperaturethe resulting mixture was refluxed for 16 h under nitrogen atmosphere
  2. extractionThe aqueous layer was extracted with additional CH2Cl2
  3. dry with materialdried over MgSO4
  4. customAfter evaporating the solvent
  5. customthe crude product was purified by column chromatography (0-35% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-a493c1928ac64963a29527eec1608833
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

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