Potassium Carbonate → 7-(1-methyl-4-(4-(methylsulfonyl)phenoxy)-1H-pyrazolo[3,4-b]pyridin-6-yl)benzo[d]isoxazol-3-amine

HRID 241975Notes

Reaction equation

HRID 241975 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[O:15][N:14]=[C:13]([NH2:17])[C:12]=3[CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]2[N:18]([CH3:21])[N:19]=[CH:20][C:3]=12.[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:21][N:18]1[C:4]2=[N:5][C:6]([C:8]3[C:16]4[O:15][N:14]=[C:13]([NH2:17])[C:12]=4[CH:11]=[CH:10][CH:9]=3)=[CH:7][C:2]([O:32][C:29]3[CH:28]=[CH:27][C:26]([S:23]([CH3:22])(=[O:25])=[O:24])=[CH:31][CH:30]=3)=[C:3]2[CH:20]=[N:19]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1233504-(Methylsulfonyl)phenolHCID 580832327-(4-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)benzo[d]isoxazol-3-amine

Product 1

HCID 462186757-(1-methyl-4-(4-(methylsulfonyl)phenoxy)-1H-pyrazolo[3,4-b]pyridin-6-yl)benzo[d]isoxazol-3-amineYield 21.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 7-(4-chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)benzo[d]isoxazol-3-amine 17 (0.032 g, 0.106 mmol), 4-methylsulfonyl phenol 8a (0.036 g, 0.213 mmol) and potassium carbonate (0.15 g, 1.06 mmol) in 2 mL DMF was heated in a microwave at 155° C. for 30 minutes. The reaction mixture was filtered, solvent removed and diluted with ethyl acetate. The organic portions were pooled and washed with saturated bicarbonate solution and brine, dried over anhydrous sodium sulfate and solvent was removed. The crude material was purified using mass directed purification to give 10 mg of 121. 1H NMR (400 MHz, DMSO) δ=8.02-7.58 (m, 8H), 7.58 (dd, J=26.9, 35.7, 2H), 6.53 (s, 1H), 4.15-4.01 (m, 3H), 3.3-3.06 (m, 3H). MS (ESI) m/z 436.0 (M+1)+

Workup

  1. filtrationThe reaction mixture was filtered
  2. customsolvent removed
  3. additiondiluted with ethyl acetate
  4. washwashed with saturated bicarbonate solution and brine
  5. dry with materialdried over anhydrous sodium sulfate and solvent
  6. customwas removed
  7. customThe crude material was purified
  8. custompurification

Sources & evidence

ORD record
ord-0b0a05b0f91f416e8cc17654c2d7f672
Source dataset
uspto-grants-2014_02
Patent number
US08653098B2

Reaction notes

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