Potassium Carbonate → 2-(4-Isopropyl-thiazol-2-yl)-6-methoxy-4-(4-methoxy-benzyloxy)-8-methyl-quinoline

HRID 530730노트

반응식

HRID 530730 반응식
[CH:1]([C:4]1[N:5]=[C:6]([Sn](CCCC)(CCCC)CCCC)[S:7][CH:8]=1)([CH3:3])[CH3:2].Cl[C:23]1[CH:32]=[C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)[C:30]2[C:25](=[C:26]([CH3:45])[CH:27]=[C:28]([O:43][CH3:44])[CH:29]=2)[N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:1]([C:4]1[N:5]=[C:6]([C:23]2[CH:32]=[C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=3)[C:30]3[C:25](=[C:26]([CH3:45])[CH:27]=[C:28]([O:43][CH3:44])[CH:29]=3)[N:24]=2)[S:7][CH:8]=1)([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 575787544-Isopropyl-2-(tributylstannyl)thiazoleHCID 866277512-Chloro-6-methoxy-4-(4-methoxybenzyloxy)-8-methyl-quinoline

생성물 1

HCID 666508822-(4-Isopropyl-thiazol-2-yl)-6-methoxy-4-(4-methoxy-benzyloxy)-8-methyl-quinoline수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Compound 219 (100 mg, 0.29 mmol), compound 221f (242 mg, 0.35 mmol), and potassium carbonate (48 mg, 0.35 mmol) in degassed anhydrous DMF were stirred under microwave radiations at 80° C. for 1 hr. Solvent was removed under reduced pressure and the crude material was purified by chromatography on silica gel (Petroleum ether/DCM) to yield compound 222f as yellow powder in 63% yield. 1H NMR (CDCl3, 400 MHz) δ 1.40 (s, 3H), 1.42 (s, 3H), 2.80 (s, 3H), 3.17-3.24 (m, 1H), 3.85 (s, 3H), 3.89 (s, 3H), 5.31 (s, 2H), 6.99 (d, J=9.10 Hz, 2H), 7.00 (s, 1H), 7.21 (m, 1H), 7.31 (d, J=2.93 Hz, 1H), 7.49 (d, J=9.10 Hz, 2H), 7.79 (s, 1H).

후처리

  1. customSolvent was removed under reduced pressure
  2. customthe crude material was purified by chromatography on silica gel (Petroleum ether/DCM)

출처 및 근거

ORD 기록
ord-e86a220ecbca4577988097076d53fdbe
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353100B2

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