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Sodium Carbonate → 2-m-Tolyl-6-(trifluoromethyl)nicotinonitrile

HRID 1428732
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HRID 1428732 반응식
Cl[C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:14]1([CH3:23])[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C1CCCCC1.C(OCC)(=O)C>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.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>[C:14]1([CH3:23])[CH:19]=[CH:18][CH:17]=[C:16]([C:2]2[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH:15]=1
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참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acidHCID 27784132-Chloro-6-(trifluoromethyl)nicotinonitrileHCID 21867204Cyclohexane ethylacetate

생성물 1

HCID 866802152-m-Tolyl-6-(trifluoromethyl)nicotinonitrile수율 49%

시약·촉매·용매 4

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

2-Chloro-6-(trifluoromethyl)nicotinonitrile (3 g, 14.56 mmol) was dissolved in toluene (70 mL) and ethanol (14 mL). m-tolylboronic acid (2.969 g, 21.814 mmol), aqueous sodium carbonate solution (2 M, 14 mL) and Pd(PPh3)4 (1.684 g, 1.456 mmol) were added. The mixture was flushed with nitrogen and stirred under microwave conditions (7 bar) at 100° C. for 2 h. The concentrated reaction mixture was cooled, diluted with ethyl acetate (200 mL), passed through celite (cyclohexane/ethyl acetate 9:1, 2×1 L) and concentrated in vacuo to afford 2-m-tolyl-6-(trifluoromethyl)nicotinonitrile (1.87 g, 49%).

후처리

  1. customThe mixture was flushed with nitrogen
  2. customThe concentrated reaction mixture
  3. temperaturewas cooled
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6f30511677c749ccbacfa832fd2b2618
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08937092B2

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