Potassium Carbonate → HCID 178454344, compound

HRID 389484Notes

Reaction equation

HRID 389484 reaction equation
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]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66760164HCID 66760164, compoundHCID 178455325HCID 178455325, compound

Product 1

HCID 178454344HCID 178454344, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-ba1ddfc935374f75b0f34c29512beed7
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

Loading…