Potassium Carbonate → HCID 58292782, compound

HRID 1798204Notes

Reaction equation

HRID 1798204 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[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=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[CH:23]=[CH:22][N:21]=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 58292555HCID 58292555, compound

Product 1

HCID 58292782HCID 58292782, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [6-(2-chloro-pyrimidin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.5 g, 1.38 mmol), 10% Pd/C (0.45 g) and K2CO3 (0.38 g, 2.75 mmol) in EtOAc (15 mL) was hydrogenated at 30 psi for 1.5 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-(pyrimidin-4-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.4 g, 88%). 1H NMR (400 MHz, DMSO): δ 9.27 (s, 1H), 8.73 (s, 1H), 8.65 (d, J=5.6 Hz, 1H), 7.26 (d, J=2.0 Hz, 1H), 7.12 (d, J=6.8 Hz, 2H), 5.54 (dd, J=2.4, 9.2 Hz, 1H), 4.04 (q, J=6.8 Hz, 2H), 3.13 (dd, J=2.4, 15.2 Hz, 1H), 2.34-2.27 (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-c9a8815f99744acf9d78bef1ff38a1b9
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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