Acetate → HCID 25119551, compound

HRID 1866065Notes

Reaction equation

HRID 1866065 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:17])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[N:26]1[CH:31]=[C:30](B(O)O)[CH:29]=[N:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C([O-])(=O)C.C(=O)([O-])O.[Na+]>COCCOC.C(O)C.O>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([C:8]2([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:30]4[CH:31]=[N:26][CH:27]=[N:28][CH:29]=4)[CH:3]=3)[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:17])=[N:9]2)=[CH:19][CH:20]=1

Participants

9

Reactant 5

HCID 175AcetateHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 57978150HCID 57978150, compound

Product 1

HCID 25119551HCID 25119551, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-(3-bromophenyl)-5-(4-methoxyphenyl)-5H-pyrrolo[3,4-b]pyridin-7-amine (Example 3, 85 mg, 0.215 mmol), pyrimidin-5-ylboronic acid (35 mg, 0.280 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (18 mg, 0.022 mmol) and cesium carbonate (210 mg, 0.645 mmol) in a mixture of 1,2-dimethoxyethane, water and ethanol (6:3:1, 5 mL) was heated by microwave irradiation at 130° C., under an argon atmosphere for 15 min. After cooling to ambient temperature the mixture was filtered, concentrated in vacuo and purified by preparative HPLC to give 22 mg (26% yield) after liberating the free base by treatment of the acetate with sodium hydrogen carbonate. 1H NMR (CDCl3) δ 9.17 (s, 1H), 8.86 (s, 2H), 8.63 (dd, 1H), 7.92 (dd, 1H), 7.55 (m, 1H), 7.48-7.40 (m, 3H), 7.36 (dd, 1H), 7.26 (m, 2H), 6.82 (m, 2H), 3.78 (s, 3H); MS (ESI) m/z 394 [M+1]+.

Workup

  1. temperatureAfter cooling to ambient temperature the mixture
  2. filtrationwas filtered
  3. concentrationconcentrated in vacuo
  4. custompurified by preparative HPLC
  5. customto give 22 mg (26% yield)

Sources & evidence

ORD record
ord-487b81152b4840428bdd785a1ac3e312
Source dataset
uspto-grants-2009_12
Patent number
US07629356B2

Reaction notes

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