Potassium Carbonate → HCID 178455334, compound

HRID 389460Notes

Reaction equation

HRID 389460 reaction equation
[Cl:1][C:2]1[O:12][C:5]2=[C:6]([NH2:11])[N:7]=[CH:8][C:9](I)=[C:4]2[CH:3]=1.[Si:13]([O:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([N:27]2[CH:31]=[C:30](B(O)O)[CH:29]=[N:28]2)[CH2:23][CH2:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[Si:13]([O:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([N:27]2[CH:31]=[C:30]([C:9]3[CH:8]=[N:7][C:6]([NH2:11])=[C:5]4[O:12][C:2]([Cl:1])=[CH:3][C:4]=34)[CH:29]=[N:28]2)[CH2:23][CH2:22]1)([C:16]([CH3:19])([CH3:17])[CH3:18])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 667601342-Chloro-4-iodofuro[2,3-c]pyridin-7-amineHCID 178455325HCID 178455325, compound

Product 1

HCID 178455334HCID 178455334, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-chloro-4-iodo-furo[2,3-c]pyridin-7-ylamine (2 g, 7 mmol), [1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]boronic acid (2.75 g, 8.49 mmol), (1,1′bis-(diphenylphosphino)-ferrocene)palladium dichloride (248 mg, 0.340 mmol) and potassium carbonate (2.35 g, 17.0 mmol) in 1,4-dioxane (20 mL) and water (9.5 mL) was heated to 70° C. for 22 h. The mixture was partitioned between ethyl acetate and water and the aqueous phase extracted with DCM. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Purification by ISCO chromatography (10% to 50% ethyl acetate:heptane) followed by trituration with ether:heptane afforded 2.0 g (60%) of the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 7.97 (s, 1 H), 7.76-7.69 (m, 1 H), 7.62 (s, 1 H), 6.73 (s, 1 H), 4.73 (s, 2 H), 4.17 (tt, J=3.9, 11.6 Hz, 1 H), 3.73 (tt, J=4.3, 10.5 Hz, 1 H), 2.23 (d, J=12.1 Hz, 2 H), 2.09-1.99 (m, 2 H), 1.91 (dq, J=3.5, 11.9 Hz, 2 H), 1.61-1.48 (m, 2 H), 0.92 (s, 9 H), 0.10 (s, 6 H); MS (ESI): 447.39, 449.35 [M+H]+.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. extractionthe aqueous phase extracted with DCM
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by ISCO chromatography (10% to 50% ethyl acetate:heptane)

Sources & evidence

ORD record
ord-449c54b53f4e430eaca457be091cda8c
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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