Potassium Carbonate → HCID 58292550, compound

HRID 1798272Notes

Reaction equation

HRID 1798272 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[N:19]=[N:20][C:21](Cl)=[CH:22][CH:23]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2].C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[N:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 58292574HCID 58292574, compound

Product 1

HCID 58292550HCID 58292550, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [6-(6-Chloro-pyridazin-3-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.5 g, 1.37 mmol), 10% Pd/C (0.45 g) and K2CO3 (0.38 g, 2.75 mmol) in EtOAc (20 mL) was hydrogenated at 30 psi for 2 hours. The mixture was filtered through a pad of celite and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (DCM:MeOH 95:5) to give [1-hydroxy-4-methyl-6-(pyridazin-3-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.35 g, 77%). 1H NMR (400 MHz, DMSO): δ 9.26 (s, 1H), 8.98 (dd, J=1.6, 4.8 Hz, 1H), 7.76-7.73 (m, 1H), 7.44 (dd, J=1.2, 8.8 Hz, 1H), 7.26 (d, J=2.4 Hz, 1H), 7.12 (d, J=1.6 Hz, 1H), 5.53 (dd, J=2.4, 9.2 Hz, 1H), 4.03 (q, J=7.2 Hz, 2H), 3.14 (dd, J=2.8, 15.6 Hz, 1H), 2.33-2.24 (m, 1H), 2.30 (s, 3H), 1.13 (t, J=7.2 Hz, 3H). MS (ESI) m/z=329 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel flash column chromatography (DCM:MeOH 95:5)

Sources & evidence

ORD record
ord-57a206069a7e483b88383bf0c7ac18a7
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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