Sodium Carbonate → HCID 178519549, compound

HRID 272012Notes

Reaction equation

HRID 272012 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[O:18])[CH:14]=[CH:15][CH:16]=3)[CH:9]=2)[NH:4][N:3]=1.[NH:25]1[CH:29]=[C:28](B(O)O)[CH:27]=[N:26]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O.C(OCC)(=O)C>[N:19]1([C:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([C:8]3[CH:9]=[C:10]4[C:2]([C:28]5[CH:29]=[N:25][NH:26][CH:27]=5)=[N:3][NH:4][C:5]4=[N:6][CH:7]=3)[CH:12]=2)=[O:18])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 177502781H-Pyrazole-4-boronic acidHCID 178519550HCID 178519550, compound

Product 1

HCID 178519549HCID 178519549, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [3-(3-iodo-1H-pyrazolo[3,4-b]pyridin-5-yl)-phenyl]-morpholin-4-yl-methanone (25 mg, 58 μmol), 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichlormethane adduct (5 mg, 6 μmol) and 1H-pyrazol-4-ylboronic acid (11 mg, 98 μmol) in acetonitrile (2 mL) and 2 M solution of sodium carbonate (1 mL) was irradiated in a Personal Chemistry Optimizer at 175° C. for 30 min. The crude reaction mixture was diluted with water (1 mL) and ethyl acetate (3 mL) and the organic phase separated, filtered and concentrated. The resulting crude mixture was then purified by mass-triggered reverse phase HPLC using a gradient of acetonitrile in water containing 0.1% of formic acid to afford morpholin-4-yl-{3-[3-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-methanone (6.2 mg, 29% yield) of as a colorless powder. 1H-NMR (500 MHz, d6-DMSO) δ 13.59 (s, 1H), 13.17 (s, 1H), 8.87 (d, 1H), 8.73 (d, 1H), 8.60 (s, br, 1H), 8.17 (s, br, 1H), 7.95 (ddd, 1H), 7.89 (t, 1H), (t, 1H), 7.59 (t, 1H), 7.43 (ddd, 1H), 3.80-3.35 (m, 8H). MS: m/z 397 [MNa+], 375 [MH+].

Workup

  1. customwas irradiated in a Personal Chemistry Optimizer at 175° C. for 30 min
  2. customThe crude reaction mixture
  3. customthe organic phase separated
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude mixture was then purified by mass-triggered reverse phase HPLC

Sources & evidence

ORD record
ord-f3537abc61ce499194b5ad6d0d0d4f01
Source dataset
uspto-grants-2008_11
Patent number
US07452993B2

Reaction notes

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