Potassium Carbonate → HCID 76281325, compound

HRID 929804Notes

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[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[C:20]#[N:21].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:20]([C:19]1[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=1[O:17][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)#[N:21]

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 2-hydroxybenzonitrile (22 mg, 0.184 mmol) and K2CO3 (30 mg, 0.22 mmol). The mixture was heated at 90° C. for 16 h and then evaporated to dryness. The residue was purified by chromatography (66-75% EtOAc/hexanes) to give 3-[4-(2-cyano-phenoxymethyl)-phenyl]-isoxazole-5-carboxylic acid amide (26 mg, 76%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.39 (br. s., 1H), 8.00 (br. s., 1H), 7.95 (d, J=8.2 Hz, 2H), 7.75 (dd, J=7.5, 1.5 Hz, 1H), 7.54-7.65 (m, 3H), 7.33 (d, J=8.5 Hz, 1H), 7.11 (t, J=7.5 Hz, 1H), 5.37 (s, 2H).

Workup

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

Sources & evidence

ORD record: ord-361b54161c3e471fbf97bf0d613e927a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296711B2

Reaction notes

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