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

HRID 925953ノート

反応式

HRID 925953 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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, 314), 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, 214), 7.79 (s, 1H).

後処理

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

出典と根拠

ORDレコード
ord-8973b437fbf9434d81057be771017c81
出典データセット
uspto-grants-2016_03
特許番号
US09284307B2

反応ノート

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