Potassium Carbonate → 6-((3-bromo-4,5-dihydroisoxazol-5-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1023183ノート

反応式

HRID 1023183 の反応式
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)[CH:2]=[CH2:3].C([O-])([O-])=O.[K+].[K+].[OH:22][N:23]=[C:24](Br)[Br:25]>CN(C=O)C.O.C(OCC)(=O)C>[Br:25][C:24]1[CH2:3][CH:2]([CH2:1][O:4][C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]3)[O:22][N:23]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromideHCID 190680326-(allyloxy)-3,4-dihydroquinolin-2(1H)-one

生成物 1

HCID 866804266-((3-bromo-4,5-dihydroisoxazol-5-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one収率 60.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 6-(allyloxy)-3,4-dihydroquinolin-2(1H)-one (1.85 g, 9.10 mmol) in DMF (20 mL) and water (5 mL), K2CO3 (3.77 g, 27.3 mmol) were added and the reaction mixture was cooled to 0° C. Hydroxycarbonimidic dibromide (3.69 g, 18.21 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with water, brine, and dried over Na2SO4. The organic layer was concentrated and the crude material purified by flash chromatography on silica gel using ethyl acetate/hexane as eluant to give 6-((3-bromo-4,5-dihydroisoxazol-5-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one as a white solid (1.8 g, 59.6%). 1HNMR: 400 MHz, DMSO-d6: δ 2.40 (q, J=7.20 Hz, 2H), 2.83 (t, J=8.00 Hz, 2H), 3.18 (dd, J=7.60, 17.60 Hz, 1H), 3.50 (dd, J=10.80, 17.40 Hz, 1H), 4.01-4.09 (m, 2H), 4.98-5.03 (m, 1H), 6.72-6.81 (m, 3H), 9.92 (s, 1H). LCMS: RT 1.408 min; LCMS (ES-API), m/z 327 (M+H).

後処理

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationThe organic layer was concentrated
  4. customthe crude material purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-af8faa75c6724bc6a10558aa66497a62
出典データセット
uspto-grants-2014_05
特許番号
US08722670B2

反応ノート

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