Sodium Carbonate → HCID 86651994, compound

HRID 1615367Notes

Reaction equation

HRID 1615367 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=2)[CH:3]=[N:2]1.[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[N:24]=[CH:23][C:22](B3OC(C)(C)C(C)(C)O3)=[CH:21][N:20]=2)[CH2:15][CH2:14]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][N:13]1[CH2:14][CH2:15][N:16]([C:19]2[N:20]=[CH:21][C:22]([C:3]3[C:4]4[C:9](=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][CH:5]=4)[NH:1][N:2]=3)=[CH:23][N:24]=2)[CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 164142282-(4-Methylpiperazino)pyrimidine-5-boronic acid pinacol esterHCID 185383681H-Indazole-6-carbaldehyde

Product 1

HCID 86651994HCID 86651994, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 1H-indazole-6-carbaldehyde (50 mg, 0.18 mmol), 2-(4-Methylpiperazin-1-yl)pyrimidine-5-boronic acid pinacol ester (70 mg, 0.22 mmol), Pd(PPh3)4 (13 mg, 0.018 mmol) and 2M Na2CO3 (0.10 mL, 0.22 mmol) in DME/H2O/EtOH (1.4 mL/0.4 mL/0.2 mL) was sealed and heated with stirring under microwave irradiation at 125° C. for 120 min. The crude reaction mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel using MeOH (5% to 10%) in DCM as the eluent to provide the title compound as a pale yellow solid (47 mg, 80%). 1H NMR (400 MHz, CD3OD) δ ppm 10.12 (s, 1H), 8.91 (s, 2H), 8.14 (s, 1H), 8.09 (d, J=8.6 Hz, 1H), 7.74 (d, J=8.4 Hz, 1H), 3.94 (t, J=4.5 Hz, 4H), 2.56 (t, J=4.9 Hz, 4H), 2.37 (s, 3H); MS ESI 323.1 (100) [M+H]+, calcd for [C17H18N6O+H]+ 323.2.

Workup

  1. customwas sealed
  2. temperatureheated
  3. customThe crude reaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-84b63b62c422442b9ba904af2abbf34a
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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