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Sodium Carbonate → Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone

HRID 2104475
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HRID 2104475 반응식
Cl[C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17].[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.CCO>[C:18]1([C:16]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:10][CH:9]=[CH:8][C:7]=3[C:12]([F:13])([F:15])[F:14])=[O:17])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 16090325[4-Chloro-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone

생성물 1

HCID 11360909Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 21863594
Toluene ethanol
용매

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온도
90 °C

실험 절차

[4-Chloro-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (compound of formula (VII)), 0.050 g, 0.15 mmol) was taken into toluene/EtOH (3 mL/0.5 mL). Then phenylboronic acid (0.30 mmol) was added followed by 2 M Na2CO3 (0.25 mL, 0.5 mmol) and finally Pd(PPh3)4 (0.009 g, 0.0075 mmol). The reaction was heated at 90° C. for 4 hours. The solvent was removed and the resulting material was purified via column chromatography using 5% ethyl acetate in hexane to elute out 0.043 g of the title compound: MS (ESI) m/z 378 ([M+H]+); Anal. Calcd for C23H14F3NO: C, 73.21; H, 3.74; N, 3.71. Found: C, 72.16; H, 3.77; N, 3.69.

후처리

  1. customThe solvent was removed
  2. customthe resulting material was purified via column chromatography
  3. washto elute out 0.043 g of the title compound

출처 및 근거

ORD 기록
ord-a22ef927741145ac8ef0414a4819d3e4
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07576215B2

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