Potassium Carbonate → HCID 23629663, compound

HRID 2375670Notes

Reaction equation

HRID 2375670 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH3:16])=[O:14].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(O)C.O>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:23]3[CH:24]=[C:19]([O:18][CH3:17])[CH:20]=[CH:21][C:22]=3[O:25][CH3:26])[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343422,5-Dimethoxyphenylboronic acidHCID 67228769HCID 67228769, compound

Product 1

HCID 23629663HCID 23629663, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

The title compound was prepared from 4-amino-8-bromo-N-methyl-cinnoline-3-carboxamide (20.0 g, 63.1 mmol) and 2,5-dimethoxyphenyl boronic acid (22.3 g, 122.4 mmol) according to Method B except that potassium carbonate was used as the base and tetrahydrofuran:ethanol:water (1:1:1) was used as the solvent system. The reaction mixture was filtered and the yellow solids were slurried in 10% methanol in chloroform and filtered. The combined filtrates were concentrated to a solid, slurried in hot ethyl acetate, and filtered. The combined solids were further purified on silica gel using 5% methanol in chloroform as the eluent. A final crystallization from refluxing ethyl acetate followed by drying under high vacuum at 45° C. afforded the title compound as a light yellow solid (12.65 g, 59%). 1H NMR (500.333 MHz, DMSO) δ 9.07 (d, J=4.6 Hz, 1H), 8.39 (d, J=8.2 Hz, 1H), 7.76-7.70 (m, 2H), 7.03 (d, J=9.1 Hz, 1H), 6.97 (dd, J=8.9, 3.0 Hz, 1H), 6.87 (d, J=3.2 Hz, 1H), 3.73 (s, 3H), 3.55 (s, 3H), 2.86 (d, J=4.8 Hz, 3H). MS APCI, m/z=xx (M+H). HPLC 2.23 min. MP=279.1-279.8.

Workup

  1. filtrationThe reaction mixture was filtered
  2. filtrationfiltered
  3. concentrationThe combined filtrates were concentrated to a solid, slurried in hot ethyl acetate
  4. filtrationfiltered
  5. customThe combined solids were further purified on silica gel using 5% methanol in chloroform as the eluent
  6. customA final crystallization
  7. temperaturefrom refluxing ethyl acetate
  8. customby drying under high vacuum at 45° C.

Sources & evidence

ORD record
ord-9b989f4f1a244e26bfd73111548f6541
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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