Water → HCID 178460611, 화합물

HRID 1852843

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HRID 1852843 반응식
Br[C:2]1[N:19]([CH2:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]2)[C:5]2[C:6]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=3)=[N:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[N:3]=1.[C:28]([Si:32]([CH3:47])([CH3:46])[O:33][CH2:34][C:35](B1OC(C)(C)C(C)(C)O1)=[CH2:36])([CH3:31])([CH3:30])[CH3:29].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Si:32]([O:33][CH2:34][C:35]([C:2]1[N:19]([CH2:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]2)[C:5]2[C:6]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=3)=[N:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[N:3]=1)=[CH2:36])([C:28]([CH3:29])([CH3:30])[CH3:31])([CH3:46])[CH3:47]

참가 물질

7

반응물 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 16069431tert-Butyl(dimethyl){[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]oxy}silaneHCID 178461197HCID 178461197, 화합물

생성물 1

HCID 178460611HCID 178460611, 화합물

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 2-bromo-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (Preparative Example 3.1; 3.0 g, 6.93 mmol) in 1,4-dioxane (60 mL), tert-butyldimethyl((2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)oxy)silane (3.09 g 10.39 mmol), potassium phosphate (2.94 g, 13.86 mmol), and water (6 mL) were added, and the mixture was degassed with argon for 15 minutes. PdCl2(dppf) (0.85 g, 1.04 mmol), was added, and the mixture was degassed with argon again for 5 minutes. The reaction was then heated at 100° C. for 16 h. The reaction mixture was cooled to room temperature, quenched with water (20 mL), and extracted with ethyl acetate (100 mL). The organic layer was separated, washed with brine (50 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography using 15% ethyl acetate/petroleum ether as eluent to yield 2-(3-{[tert-butyl(dimethyl)silyl]oxy}prop-1-en-2-yl)-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ES/APCI calcd. for C29H38ClN5OSi [M+H]+ 536. found 536.

후처리

  1. customthe mixture was degassed with argon for 15 minutes
  2. customthe mixture was degassed with argon again for 5 minutes
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customquenched with water (20 mL)
  5. extractionextracted with ethyl acetate (100 mL)
  6. customThe organic layer was separated
  7. washwashed with brine (50 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-5a1d5477b1164c1b9699aaf4681877b0
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962611B2

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