Potassium Carbonate → HCID 178454344, 화합물

HRID 389484노트

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HRID 389484 반응식
I[C:2]1[CH:7]=[N:6][C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:4]2[O:23][CH:24]=[CH:25][C:3]=12.[Si:26]([O:33][C@H:34]1[CH2:39][CH2:38][C@H:37]([N:40]2[CH:44]=[C:43](B(O)O)[CH:42]=[N:41]2)[CH2:36][CH2:35]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[Si:26]([O:33][C@H:34]1[CH2:39][CH2:38][C@H:37]([N:40]2[CH:44]=[C:43]([C:2]3[CH:7]=[N:6][C:5]([N:8]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])=[C:4]4[O:23][CH:24]=[CH:25][C:3]=34)[CH:42]=[N:41]2)[CH2:36][CH2:35]1)([C:29]([CH3:32])([CH3:30])[CH3:31])([CH3:28])[CH3:27]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 66760164HCID 66760164, 화합물HCID 178455325HCID 178455325, 화합물

생성물 1

HCID 178454344HCID 178454344, 화합물수율 72.2%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

A mixture of di-tert-butyl (4-iodofuro[2,3-c]pyridin-7-yl)imidodicarbonate (1.2 g, 2.6 mmol), [1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]boronic acid (1.06 g, 3.26 mmol), 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloride dichloromethane complex (213 mg, 0.261 mmol) and potassium carbonate (0.901 g, 6.52 mmol) in 1,4-dioxane (10 mL) and water (5 mL) was degassed with nitrogen for 10 min. The mixture was then heated to 70° C. for 20 min. Ethyl acetate was added, and the layers separated. The combined organic fractions were dried over sodium sulfate, filtered, and concentrated. Purification of the residue by ISCO chromatography (0% to 35% EtOAc:heptane) afforded 1.15 g (72%) of the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 8.38 (s, 1 H), 7.89 (s, 1 H), 7.82-7.77 (m, 2 H), 7.02 (d, J=2.0 Hz, 1 H), 4.21 (tdd, J=3.9, 7.7, 11.5 Hz, 1 H), 3.82-3.66 (m, 1 H), 2.33-2.17 (m, 2 H), 2.09-2.01 (m, 2 H), 2.00-1.87 (m, 2 H), 1.59-1.49 (m, 2 H), 1.40 (s, 18 H), 0.91 (s, 9 H), 0.09 (s, 6 H); MS (ESI): 613.46 [M+H]+.

후처리

  1. customwas degassed with nitrogen for 10 min
  2. additionEthyl acetate was added
  3. customthe layers separated
  4. dry with materialThe combined organic fractions were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by ISCO chromatography (0% to 35% EtOAc:heptane)

출처 및 근거

ORD 기록
ord-ba1ddfc935374f75b0f34c29512beed7
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08378104B2

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