Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate → tert-Butyl 4-(((4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinolin-7-yl)oxy)methyl)piperidine-1-carboxylate

HRID 15520

반응식

HRID 15520 반응식
Br.[F:2][C:3]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:4]=1[O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([OH:18])=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]=[CH:8][CH:7]=1.CS(O[CH2:31][CH:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]1)(=O)=O>CN(C=O)C>[F:2][C:3]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:4]=1[O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:31][CH:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[CH2:34][CH2:33]3)=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]=[CH:8][CH:7]=1

참가 물질

4

반응물 2

HCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylateHCID 1363478464-(2-fluoro-4-nitrophenoxy)-6-methoxyquinolin-7-ol HBr salt

생성물 1

HCID 59342475tert-Butyl 4-(((4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinolin-7-yl)oxy)methyl)piperidine-1-carboxylate수율 62%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
82.5 °C

실험 절차

To a mixture of 4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinolin-7-ol HBr salt (1.0 g, 2.4 mmol) and K2SO3 (2.5 g) in DMF (15 mL) at rt was added tert-butyl 4-((methylsulfonyloxy)methyl)piperidine-1-carboxylate (1.0 g, 3.4 mmol, and the reaction mixture was heated at 80-85° C. for 4 h. This mixture was directly purified by flash column chromatography on silica gel eluting with hexane:EtOAc/600:400, and then 300:700 to obtain the desired product (786 mg, 62%) as a glassy solid material. 1H NMR (CDCl3) δ 8.57 (d, 1H, J=5.0 Hz), 8.20 (dd, 1H, J=9.9, 2.8 Hz), 8.13 (dd, 1H, J=8.8, 1.7 Hz), 7.43 (d, 2H, J=2.2 Hz), 7.33 (t, 1H, J=7.7 Hz), 6.54 (d, 1H, J=5.0 Hz), 4.20 (m, 2H), 4.04 (d, 2H, J=6.6 Hz), 4.00 (s, 3H), 2.77 (m, 2H), 2.19-1.89 (m, 3H), 1.47 (s, 9H), 1.34 (m, 2H).

후처리

  1. customThis mixture was directly purified by flash column chromatography on silica gel eluting with hexane

출처 및 근거

ORD 기록
ord-d3e2c40ac4624baaa37c1660002f5d98
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732613B2

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