Dichloromethane → HCID 178492925, compound

HRID 1484312Notes

Reaction equation

HRID 1484312 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[C:15]([O:22][CH3:23])[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].ClCCl>CN(C=O)C.C(O)C.O>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[N:8][C:9]=3[NH2:11])[NH:4][N:3]=2)=[C:15]([O:22][CH3:23])[CH:14]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 178508725HCID 178508725, compound

Product 1

HCID 178492925HCID 178492925, compoundYield 35.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1.00 g, 3.83 mmoles) in DMF (14 ml), ethanol (7 ml) and water (7 ml), 4-fluoro-2-methoxyphenyl boronic acid (0.846 g, 4.979 mmoles) and sodium carbonate (2.06 g, 19.15 mmoles) were added and the system is degassed for 30 min. Tetrakis triphenylphosphine Palladium (0.754 g, 0.652 mmoles) was added under nitrogen atmosphere and heated to 80° C. After 12 h, the reaction mixture was celite filtered, concentrated and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol:dichloromethane to afford the title compound as off-white solid (0.350 g, 35% yield). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 13.46 (s, 1H), 8.14 (s, 1H), 7.40 (t, J=8.4 Hz, 1H), 7.09 (dd, J=11.5, 2.9 Hz, 1H), 6.91 (dt, J=8.4, 2.4 Hz 1H), 3.78 (s, 3H).

Workup

  1. customthe system is degassed for 30 min
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-f177e2959274487a93b43afa935ad7a1
Source dataset
uspto-grants-2016_08
Patent number
US09421209B2

Reaction notes

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