Cesium carbonate → tert-butyl 3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate

HRID 1943890노트

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HRID 1943890 반응식
Br[C:2]1[CH:3]=[C:4]2[C:10]([O:11][CH3:12])=[N:9][N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:5]2=[N:6][CH:7]=1.[C:22](=[O:29])([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[NH2:23].C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C1COCC1.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]>[CH3:12][O:11][C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([NH:23][C:22](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:3]=2)[N:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:9]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 670888295-bromo-3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine

생성물 1

HCID 67089104tert-butyl 3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate수율 24.8%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

5-Bromo-3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine (0.109 g, 0.313 mmol), tert-butyl carbamate (0.110 g, 0.939 mmol), Cs2CO3 (0.153 g, 0.470 mmol), Pd2 dba3*CHCl3 (0.0324 g, 0.0313 mmol) and 4,5-bis(diphenylphosphino)-9,9 dimethylxanthene (0.0362 g, 0.0626 mmol) were taken up in THF, degassed with argon for 15 minutes, and heated to reflux overnight. The solution was partitioned between water and EtOAc. The organic portion was washed with water (3×), brine, dried over Na2SO4 and concentrated to an oil which was purified by column chromatography (4:1 hexane/EtOAc) to give tert-butyl 3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate (0.0298 g, 24.8%) as an oil.

후처리

  1. customdegassed with argon for 15 minutes
  2. temperatureheated
  3. temperatureto reflux overnight
  4. customThe solution was partitioned between water and EtOAc
  5. washThe organic portion was washed with water (3×), brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to an oil which
  8. customwas purified by column chromatography (4:1 hexane/EtOAc)

출처 및 근거

ORD 기록
ord-4361c26ced224f75b46778539bcdbf7f
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394795B2

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