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Tri-o-tolylphosphine → 2-[3-(2-Fluoropyridin-4-yl)benzyl]pyrazolo[1,5-a]quinazolin-5(4h)-one

HRID 1927288
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HRID 1927288 반응식
Br[C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][C:6]1[CH:19]=[C:9]2[NH:10][C:11](=[O:18])[C:12]3[C:17]([N:8]2[N:7]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3.[F:23][C:24]1[CH:29]=[C:28]([Sn](CCCC)(CCCC)CCCC)[CH:27]=[CH:26][N:25]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.CCOC(C)=O.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]>[F:23][C:24]1[CH:29]=[C:28]([C:2]2[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=2)[CH2:5][C:6]2[CH:19]=[C:9]3[NH:10][C:11](=[O:18])[C:12]4[C:17]([N:8]3[N:7]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:27]=[CH:26][N:25]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 80271Tri-o-tolylphosphineHCID 164270992-Fluoro-4-(tributylstannyl)pyridineHCID 1359396462-(3-Bromobenzyl)pyrazolo[1,5-a]quinazolin-5(4h)-one

생성물 1

HCID 1359396522-[3-(2-Fluoropyridin-4-yl)benzyl]pyrazolo[1,5-a]quinazolin-5(4h)-one

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium
촉매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

실험 절차

A mixture of Example 61B (0.1 g, 0.282 mmol), 2-fluoro-4-(tributylstannyl)pyridine (0.11 g, 0.285 mmol) triethylamine (0.11 g, 1.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.039 g, 0.01 mmol) and tri-o-tolylphosphine (0.007 g, 0.023 mmol) in DMF (2 mL) was heated at 100° C. for 6 hr. The mixture was diluted with EtOAc and washed with sat NaHCO3, H2O and brine, then evaporated. The residue was purified by chromatography on silica gel with 20% to 80% ethylacetate in hexane to provide the desired product. 1H NMR (500 MHz, DMSO-d6) δ ppm 4.10 (s, 2 H) 5.75 (s, 1 H) 7.44-7.53 (m, 4 H) 7.68-7.74 (m, 2 H) 7.83-7.88 (m, 2 H) 8.04 (d, J=8.24 Hz, 1 H) 8.11 (d, J=6.71 Hz, 1 H) 8.30 (d, J=5.49 Hz, 1 H).

후처리

  1. washwashed
  2. customevaporated
  3. customThe residue was purified by chromatography on silica gel with 20% to 80% ethylacetate in hexane

출처 및 근거

ORD 기록
ord-6af189e2b25744bb99e73e3ccca36c11
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183250B2

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