2-Tert-Butylphenol → HCID 76281323, compound

HRID 929802Notes

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.[C:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[OH:27])([CH3:20])([CH3:19])[CH3:18].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][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)([CH3:20])([CH3:18])[CH3:19]

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-tert-butylphenol (28 μL, 0.182 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-tert-butyl-phenoxymethyl)-phenyl]-isoxazole-5-carboxylic acid amide (28 mg, 75%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.39 (s, 1H), 8.02 (s, 1H), 7.95 (d, J=8.5 Hz, 2H), 7.57-7.67 (m, 2H), 7.12-7.28 (m, 2H), 7.00-7.09 (m, 1H), 6.82-6.94 (m, 1H), 5.20 (s, 2H), 1.34 (s, 9H).

Workup

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

Sources & evidence

ORD record: ord-3d0e44f6eab6465eb59feb1db234d2c2
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296711B2

Reaction notes

Loading…