1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 5-(4-((t-Butyldimethylsilyloxy)methyl)piperidin-1-yl)-2-chloropyridine

HRID 876000

반응식

HRID 876000 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.[Si:9]([O:16][CH2:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].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.CC(C)([O-])C.[Na+]>O1CCOCC1.C(OCC)(=O)C.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]>[Si:9]([O:16][CH2:17][CH:18]1[CH2:19][CH2:20][N:21]([C:2]2[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=2)[CH2:22][CH2:23]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

참가 물질

8

반응물 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27344145-Bromo-2-chloropyridineHCID 23676156Sodium t-butoxideHCID 670219944-{[(Tert-butyldimethylsilyl)oxy]methyl}piperidine

생성물 1

HCID 582995615-(4-((t-Butyldimethylsilyloxy)methyl)piperidin-1-yl)-2-chloropyridine수율 9%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

5-Bromo-2-chloropyridine (1.00 g, 5.20 mmol), 4-((t-butyldimethylsilyloxy)-methyl)piperidine (284), (1.19 g, 5.20 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.0952 g, 0.104 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.180 g, 0.312 mmol), and sodium t-butoxide (0.749 g, 7.79 mmol) were dissolved in 40 mL dioxane under argon. The reaction was heated at 80° C. for 17 hours. The resulting solution was cooled an taken up in ethyl acetate (125 mL) and washed with aqueous K2CO3, (10%, 100 mL) water (100 mL1), and brine (100 mL). The organic phase was dried (MgSO4) and evaporated to give an orange oil. Silica gel chromatography (gradient elution hexanes/0-10% ethyl acetate) afforded compound 281 as a white solid (158 mg, 9%).

후처리

  1. temperatureThe resulting solution was cooled
  2. washwashed with aqueous K2CO3, (10%, 100 mL) water (100 mL1), and brine (100 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. customto give an orange oil
  6. washSilica gel chromatography (gradient elution hexanes/0-10% ethyl acetate)

출처 및 근거

ORD 기록
ord-28edc2b091c242b9b9d7501774b6b931
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980903B2

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