Methyl Acrylate → 3-{4-[2-(6-Methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo [1,2-b]pyrazol-3-yl]-quinolin-7-yl}-acrylic Acid Methyl Ester

HRID 8252

반응식

HRID 8252 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=4)=[N:15][N:14]4[CH2:24][CH2:25][CH2:26][C:13]=34)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(N(CCCC)CCCC)CCC.[C:40]([O:44][CH3:45])(=[O:43])[CH:41]=[CH2:42].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].CN(C)C=O>[CH3:45][O:44][C:40](=[O:43])[CH:41]=[CH:42][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=4)=[N:15][N:14]4[CH2:24][CH2:25][CH2:26][C:13]=34)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 7294Methyl AcrylateHCID 7622TributylamineHCID 80271Tri-o-tolylphosphine2회HCID 219925227-Bromo-4-(2-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinoline

생성물 1

HCID 666794803-{4-[2-(6-Methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo [1,2-b]pyrazol-3-yl]-quinolin-7-yl}-acrylic Acid Methyl Ester

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매2회HCID 1140Toluene용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

Nitrogen is bubbled through a solution of 7-bromo-4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline (0.050 g, 0.12 mmol), tributylamine (0.032 mL, 0.17 mmol), methyl acrylate (0.027 mL, 0.24 mmol), and N,N-dimethylformamide (0.5 mL) in toluene (1.0 mL) for 20 min. Pd(OAc)2 (0.002 g, 0.006 mmol) and tri(o-tolyl)phosphine (0.007 g, 0.021 mmol) are added and nitrogen bubbled through the reaction mixture for 10 min. The mixture is heated to 80° C. for 24 h. An additional portion of Pd(OAc)2 (0.002 g, 0.006 mmol) and tri(o-tolyl)phosphine (0.007 g, 0.021 mmol) is added and heating continues for another 24 h. The reaction is cooled and concentrated in vacuo and the residue chromatographed on SiO2 (2% methanol in methylene choloride) to yield the title compound, 0.49 g (97%), as a yellowish solid.

후처리

  1. customnitrogen bubbled through the reaction mixture for 10 min
  2. temperatureheating
  3. temperatureThe reaction is cooled
  4. concentrationconcentrated in vacuo
  5. customthe residue chromatographed on SiO2 (2% methanol in methylene choloride)

출처 및 근거

ORD 기록
ord-e7e385e0055b4b74a462f5b25feca342
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087626B2

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