Potassium Fluoride → 4-(4-Chloro-2-methylphenyl)-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile

HRID 1472772노트

반응식

HRID 1472772 반응식
Br[C:2]1[CH:3]=[C:4]([C:18]#[N:19])[S:5][C:6]=1[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:17])=[CH:9][CH:8]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[C:23]([CH3:30])[CH:22]=1.[F-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:3]=[C:4]([C:18]#[N:19])[S:5][C:6]=2[C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:17])=[CH:9][CH:8]=2)=[C:23]([CH3:30])[CH:22]=1

참가 물질

5

반응물 3

HCID 522689Potassium FluorideHCID 5017600(4-Chloro-2-methylphenyl)boronic acidHCID 682936224-Bromo-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile

생성물 1

HCID 682936984-(4-Chloro-2-methylphenyl)-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile수율 90.6%

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

실험 절차

A round-bottomed flask was charged with 4-bromo-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile (203 mg, 0.62 mmol), 4-chloro-2-methylphenylboronic acid (119 mg, 0.70 mmol), Pd2(dba)3 (9.2 mg, 0.010 mmol) and KF (126 mg, 2.17). After degassed, dioxane (2.0 mL) and P(Bu-t)3 (0.15 mL, 0.2M, 0.03 mmol) was added. The reaction mixture was stirred at rt until complete. 20 mL of water was added, and the reaction mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by flash chromatography (hexane:CH2Cl2=3:1). 0.21 g (90.6%) of product was obtained as a white solid.

후처리

  1. customAfter degassed
  2. additiondioxane (2.0 mL) and P(Bu-t)3 (0.15 mL, 0.2M, 0.03 mmol) was added
  3. addition20 mL of water was added
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (hexane:CH2Cl2=3:1)

출처 및 근거

ORD 기록
ord-cad9fe2fa4a04c468171590c5702b5e0
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012655B2

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