Cesium carbonate → HCID 86684529, 화합물

HRID 593070

반응식

HRID 593070 반응식
[CH3:1][CH:2]1[N:7]([CH3:8])[CH2:6][CH2:5][N:4]2[N:9]=[C:10]([NH2:12])[CH:11]=[C:3]12.[C:13]([O:16][CH2:17][C:18]1[C:19]([N:33]2[CH2:44][CH2:43][N:42]3[C:35](=[CH:36][C:37]4[CH2:38][C:39](C)([CH3:45])[CH2:40][C:41]=43)[C:34]2=[O:47])=[N:20][CH:21]=[CH:22][C:23]=1[C:24]1[CH:29]=[C:28](Br)[C:27](=[O:31])[N:26]([CH3:32])[CH:25]=1)(=[O:15])[CH3:14].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>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].O1CCOCC1>[C:13]([O:16][CH2:17][C:18]1[C:19]([N:33]2[CH2:44][CH2:43][N:42]3[C:41]4[CH2:40][CH2:39][CH2:45][CH2:38][C:37]=4[CH:36]=[C:35]3[C:34]2=[O:47])=[N:20][CH:21]=[CH:22][C:23]=1[C:24]1[CH:29]=[C:28]([NH:12][C:10]2[CH:11]=[C:3]3[CH:2]([CH3:1])[N:7]([CH3:8])[CH2:6][CH2:5][N:4]3[N:9]=2)[C:27](=[O:31])[N:26]([CH3:32])[CH:25]=1)(=[O:15])[CH3:14]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86684396[4-(5-Bromo-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridin-3-yl]methyl AcetateHCID 866845274,5-Dimethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amine

생성물 1

HCID 86684529HCID 86684529, 화합물수율 82%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A 25-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 287i (20 mg, 1.0 eq., 0.12 mmol), (4-(5-bromo-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)pyridin-3-yl)methyl acetate 273a (127 mg, 2.0 eq., 0.24 mmol), Pd2(dba)3 (9.0 mg, 0.1 eq., 0.010 mmol), Xantphos (11 mg, 0.2 eq., 0.020 mmol), Cs2CO3 (78 mg, 2.0 eq., 0.24 mmol), and dioxane (5 mL). After three cycles of vacuum/N2 flush, the mixture was stirred at 100° C. for 2 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with 20:1 dichloromethane/methanol to afford 287j as a brown solid (60 mg, 82%). MS-ESI: [M+H]+ 610.9

후처리

  1. customA 25-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customAfter three cycles of vacuum/N2 flush
  3. temperatureIt was then cooled to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica-gel column chromatography
  7. washeluting with 20:1 dichloromethane/methanol

출처 및 근거

ORD 기록
ord-a735605f0b644b37b2a2dcb24d2e37da
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238655B2

연결된 노트

불러오는 중…