2-Isopropylphenol → HCID 76281320, compound

HRID 929799Notes

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

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-isopropylphenol (25 μL, 0.185 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-isopropyl-phenoxymethyl)-phenyl]-isoxazole-5-carboxylic acid amide (28 mg, 78%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.39 (br. s., 1H), 8.01 (br. s., 1H), 7.93 (d, J=8.1 Hz, 2H), 7.55-7.65 (m, 3H), 7.21 (dd, J=7.5, 1.6 Hz, 1H), 7.06-7.17 (m, 1H), 7.01 (d, J=7.3 Hz, 1H), 6.84-6.96 (m, 1H), 5.18 (s, 2H), 3.22-3.39 (m, 3H, including water peak), 1.18 (d, J=7.0 Hz, 6H).

Workup

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

Sources & evidence

ORD record: ord-c89274758dcd4a6f95ce6c1d8e908da2
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296711B2

Reaction notes

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