Potassium Carbonate → HCID 76281597, compound

HRID 929811Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([C:14]([NH2:16])=[O:15])[O:11][N:10]=2)=[CH:5][CH:4]=1.[OH:17][C:18]1[C:19]([CH3:24])=[N:20][CH:21]=[CH:22][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:24][C:19]1[C:18]([O:17][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:13]=[C:12]([C:14]([NH2:16])=[O:15])[O:11][N:10]=3)=[CH:5][CH:4]=2)=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 3-(4-bromomethyl-phenyl)-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 14; 30 mg, 0.107 mmol) in CH3CN (2 mL) were added 3-hydroxy-2-methylpyridine (20 mg, 0.18 mmol) and K2CO3 (30 mg, 0.22 mmol). The mixture was heated at 90° C. overnight and then evaporated to dryness. The residue was purified by chromatography (66-75% EtOAc/hexanes) to give 3-[4-(2-methyl-pyridin-3-yloxymethyl)-phenyl]-isoxazole-5-carboxylic acid amide (12 mg, 36%) as a white powder. 1H NMR (DMSO-d6) δ ppm 8.37 (br. s., 1H), 8.00 (dd, J=4.7, 1.1 Hz, 2H), 7.93 (d, J=8.5 Hz, 2H), 7.54-7.65 (m, 3H), 7.34-7.43 (m, 1H), 7.17 (dd, J=8.5, 4.8 Hz, 1H), 5.23 (s, 2H), 2.41 (s, 3H).

Workup

customevaporated to dryness
customThe residue was purified by chromatography (66-75% EtOAc/hexanes)

Sources & evidence

ORD record: ord-afb2db97ac5d407c875f932577a28f9d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296711B2

Reaction notes

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