Triethylamine → 6-bromo-3-(4-chlorophenoxy)-4-(trifluoromethyl)quinolin-2(1H)-one

HRID 623961노트

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HRID 623961 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9](=O)[C:10]([F:13])([F:12])[F:11].[Cl:15][C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22](Cl)=[O:23])=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl>[Br:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:22](=[O:23])[C:21]([O:20][C:19]1[CH:25]=[CH:26][C:16]([Cl:15])=[CH:17][CH:18]=1)=[C:9]2[C:10]([F:13])([F:12])[F:11]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 77771p-Chlorophenoxyacetyl chlorideHCID 468388021-(2-Amino-5-bromophenyl)-2,2,2-trifluoroethanone2회

생성물 1

HCID 867154486-bromo-3-(4-chlorophenoxy)-4-(trifluoromethyl)quinolin-2(1H)-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a solution of 1-(2-amino-5-bromophenyl)-2,2,2-trifluoroethanone (2.76 g, 10.3 mmol, Intermediate 7, step b) in dichloromethane (20 mL) was added commercially available 2-(4-chlorophenoxy)acetyl chloride (2.11 g, 10.3 mmol). The resulting white solution was cooled with an ice bath to 0° C. and treated with triethylamine (4.29 mL, 30.9 mmol) dropwise. The reaction mixture was stirred at room temperature for 12 hours and at 60° C. for 2 hours. The mixture was diluted with dichloromethane at room temperature and washed with water. The organic phase was dried (MgSO4), filtered and concentrated. The residue was purified by flash column chromatography (silica gel, 25% EtOAc-Heptane), affording the title compound.

후처리

  1. washwashed with water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica gel, 25% EtOAc-Heptane)

출처 및 근거

ORD 기록
ord-2f6339c8b1f541a1beaa4dda377f1004
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303015B2

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