Potassium Phosphate, Tribasic → 7-(2,4,6-Trimethylphenyl)-N,N,2-triethylpyrazolo[1,5-a]pyridin-3-amine

HRID 859137

반응식

HRID 859137 반응식
[CH2:1]([N:3]([CH2:14][CH3:15])[C:4]1[CH:5]=[N:6][N:7]2[C:12](I)=[CH:11][CH:10]=[CH:9][C:8]=12)[CH3:2].[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:36]1(P(C2CCCCC2)C2C=CC=CC=2C2C3C(C4C=CC=CC=4C=2)=CC=CC=3)CCCC[CH2:37]1>C1(C)C=CC=CC=1.C(Cl)Cl.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]>[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[C:12]1[N:7]2[N:6]=[C:5]([CH2:36][CH3:37])[C:4]([N:3]([CH2:14][CH3:15])[CH2:1][CH3:2])=[C:8]2[CH:9]=[CH:10][CH:11]=1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 2921842,4,6-Trimethylbenzeneboronic acid2회HCID 22147288Dicyclohexyl(2-(phenanthren-9-yl)phenyl)phosphaneHCID 858677663-Diethylamino-7-iodopyrazolo[1,5-a]pyridine

생성물 1

HCID 587643137-(2,4,6-Trimethylphenyl)-N,N,2-triethylpyrazolo[1,5-a]pyridin-3-amine수율 550.3%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매2회HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 3-diethylamino-7-iodopyrazolo[1,5-a]pyridine (0.074 g, 0.217 mmol), 2,4,6-trimethylphenylboronic acid (0.053 g, 0.325 mmol), potassium phosphate (0.138 g, 0.650 mmol), dicyclohexyl[2-(9-phenanthryl)phenyl]phosphine (0.012 g, 0.026 mmol) and Pd2(dba)3 (0.004 g, 0.004 mmol) in toluene (2.2 mL) was refluxed for 72 h. Additional Pd2(dba)3 (0.004 g, 0.004 mmol) and 2,4,6-trimethylphenylboronic acid (0.053 g, 0.325 mmol) were added and reflux was continued for 42 h. The reaction mixture was diluted with CH2Cl2 and filtered through a bed of celite. The filtrate was concentrated in vacuo to dryness. The residue was subjected to preparative thin layer chromatography (5% ethyl acetate/hexane) to give 0.048 g (66%) of a light yellow oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.37 (d, J=8.9 Hz, 1H), 6.95–6.90 (m, 3H), 6.35 (d, J=6.7 Hz, 1H), 3.07 (q, J=7.1 Hz, 4H), 2.66 (q, J=7.6 Hz, 2H), 2.28 (s, 3H), 1.92 (s, 6H), 1.10 (t, J=7.6 Hz, 3H), 0.90 (t, J=7.1 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 155.6, 137.9, 137.2, 136.6, 135.5, 132.9, 130.0, 127.5, 127.4, 125.0, 124.1, 121.4, 119.7, 117.6, 112.8, 50.3, 20.2, 14.7, 14.5; IR (diffuse reflectance) 2969, 2931, 2898, 2869, 2815, 1627, 1613, 1552, 1524, 1498, 1475, 1456, 1445, 1339, 1306, 1228, 1217, 848, 782 cm−1; MS (EI) m/z 336 (M++H); HRMS (FAB) calcd for C22H29N3+H 336.2440. found 336.2421.

후처리

  1. temperaturewas refluxed for 72 h
  2. temperaturereflux
  3. filtrationfiltered through a bed of celite
  4. concentrationThe filtrate was concentrated in vacuo to dryness

출처 및 근거

ORD 기록
ord-6fba5480d1c44dc4842098a6bd92d92c
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07151109B2

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