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Cesium fluoride → 4-(5-(1-Ethoxyvinyl)-2-fluoropyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

HRID 1812376
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HRID 1812376 반응식
Cl[C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH2:16])[N:10]=2)[C:5]([F:8])=[N:6][CH:7]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[F-].[Cs+].C([Sn](CCCC)(CCCC)[C:58]([O:60][CH2:61][CH3:62])=[CH2:59])CCC>O1CCOCC1.CN(C=O)C.C(O[Pd]OC(=O)C)(=O)C>[CH2:61]([O:60][C:58]([C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH2:16])[N:10]=2)[C:5]([F:8])=[N:6][CH:7]=1)=[CH2:59])[CH3:62]
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참가 물질

8

반응물 4

HCID 25953Cesium fluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 666118184-(5-Chloro-2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

생성물 1

HCID 666118404-(5-(1-Ethoxyvinyl)-2-fluoropyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine수율 64.7%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

A mixture of 4-(5-chloro-2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (273 mg, 1.14 mmol), X-Phos (50 mg, 0.11 mmol), diacetoxypalladium (24 mg, 0.11 mmol), cesium fluoride (519 mg, 3.42 mmol) and tributyl(1-ethoxyvinyl)stannane (0.54 mL, 1.60 mmol) in 1,4-dioxane (4 mL) and DMF (1 mL) was heated in a microwave at 120° C. for 1 h. The reaction mixture was passed through a short path of a neutral alumina column, eluted with 50 mL of DCM followed by 150 mL of EtOAc. The fractions containing the desired mass [m/z (ESI, positive ion) 276.0 (M+H)+] were collected and concentrated to give the title compound (203 mg, 64.7% yield) as an off white crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.60 (2 H, m), 7.67 (2 H, m), 4.93 (1 H, d, J=3.1 Hz), 4.67 (1 H, d, J=3.1 Hz), 3.95 (2H, m), 2.38 (3 H, s), 1.11 (3 H, m). m/z (ESI, positive ion) 276.0 (M+H)+.

후처리

  1. washeluted with 50 mL of DCM
  2. additionThe fractions containing the desired mass [m/z (ESI, positive ion) 276.0 (M+H)+]
  3. customwere collected
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8b43708770f7423780c8972c17c729db
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362241B2

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