Sodium hydride → 1-((4,4-Dimethylcyclohexyl)oxy)-5-nitroisoquinoline

HRID 1469752

반응식

HRID 1469752 반응식
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:15][C:16]1([CH3:23])[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][CH2:17]1.[H-].[Na+]>C1COCC1>[CH3:15][C:16]1([CH3:23])[CH2:21][CH2:20][CH:19]([O:22][C:2]2[C:11]3[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][N:3]=2)[CH2:18][CH2:17]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 136735Cyclohexanol, 4,4-dimethyl-HCID 4597741-Chloro-5-nitroisoquinoline

생성물 1

HCID 866922441-((4,4-Dimethylcyclohexyl)oxy)-5-nitroisoquinoline수율 62.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The title compounds were prepared following the procedure described in step-1, Intermediate-10 using 1-chloro-5-nitroisoquinoline (Intermediate-1, step-1, 200 mg, 0.96 mmol) and 4,4-dimethylcyclohexanol (135 mg, 1.05 mmol) and NaH (42 mg, 1.05 mmol, 60% in mineral oil) in THF (10 mL) to afford 180 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.65 (d, J=7.8 Hz, 1H), 8.47 (d, J=7.8 Hz, 1H), 8.18 (d, J=6.6 Hz, 1H), 7.94 (d, J=6.3 Hz, 1H), 7.06 (d, J=7.8 Hz, 1H), 5.33 (m, 1H), 2.04-1.96 (m, 2H), 1.87-1.80 (m, 2H), 1.43-1.39 (m, 4H), 1.02 (s, 3H), 0.99 (s, 3H).

출처 및 근거

ORD 기록
ord-aaf83c6a7a264cfeb5e442558cf85d83
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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