Sodium Carbonate → HCID 22477279, compound

HRID 549030Notes

Reaction equation

HRID 549030 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:21][C:16]3=[N:17][CH:18]=[CH:19][N:20]=[C:15]3[CH:14]=2)=[CH:9][CH:8]=1)(=O)=O.[O:24]1[CH2:29][CH2:28]O[CH2:26][CH2:25]1.O1C=CC=C1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>CO.C(OCC)(=O)C>[O:24]1[CH:29]=[CH:28][CH:26]=[C:25]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:21][C:16]3=[N:17][CH:18]=[CH:19][N:20]=[C:15]3[CH:14]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2734357Furan-2-boronic acidHCID 22477192HCID 22477192, compound

Product 1

HCID 22477279HCID 22477279, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 6-(4-trifluoromethanesulfonyloxyphenyl)-5H-pyrrolo[2,3-b]pyrazine [20 mg, Reference Example 18(e)], dioxane (2.5 mL), furan-2-boronic acid (9.8 mg), sodium carbonate solution (0.06 mL, 2N), and tetrakis(triphenylphosphine)palladium[0] (4 mg) was heated at 180° C. in a microwave oven for 40 minutes. The reaction mixture was then evaporated and the residue was subjected to chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:1, v/v) to give, after trituration with a mixture of ethyl acetate and methanol, the title compound (7 mg) as a yellow solid. MS: 262.1 (MH+). RT=3.05 minutes.

Workup

  1. customThe reaction mixture was then evaporated
  2. additionthe residue was subjected to chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:1
  3. customv/v) to give

Sources & evidence

ORD record
ord-851378be649e4d31a21cbd7e0bc0b40c
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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