Methanol → 3-phenyl-4-(trifluoromethyl)-5-(7-vinyl-4,5-dihydro-2H-benzo[g] indazol-3-yl)isoxazole

HRID 1506364Notes

Reaction equation

[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([CH:18]3[CH2:27][CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([CH:28]=[CH2:29])[CH:24]=4)[C:19]3=O)=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.O.[NH2:34][NH2:35]>O1CCOCC1>[C:1]1([C:7]2[C:11]([C:12]([F:13])([F:15])[F:14])=[C:10]([C:16]3[NH:34][N:35]=[C:19]4[C:18]=3[CH2:27][CH2:26][C:25]3[CH:24]=[C:23]([CH:28]=[CH2:29])[CH:22]=[CH:21][C:20]4=3)[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To 2-(3-phenyl-4-(trifluoromethyl)isoxazole-5-carbonyl)-6-vinyl-3,4-dihydronaphthalen-1(2H)-one (Preparation 22A, 0.25 g, 0.608 mmol) in a 50 mL round bottom flask was added methanol (2 mL) followed by hydrazine hydrate (0.040 mL, 0.790 mmol) at room temperature. Dioxane (2 mL) was added and the homogenous reaction mixture was heated at 90° C. for 1 h. The reaction mixture was stirred at room temperature for 14 h, concentrated under reduced pressure, azeotroped with methanol (2×10 mL, water bath heated to ˜60° C.) and kept under high vacuum for 15 min to yield 3-phenyl-4-(trifluoromethyl)-5-(7-vinyl-4,5-dihydro-2H-benzo[g]indazol-3-yl)isoxazole (0.24 g, 0.454 mmol, 74.6% yield) as a thick oil. LC/MS M+1=408.1.

Workup

concentrationconcentrated under reduced pressure
customazeotroped with methanol (2×10 mL, water bath heated to ˜60° C.)
waitkept under high vacuum for 15 min

Sources & evidence

ORD record: ord-07208921eced46c69d46de005140cbfa
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216972B2

Reaction notes

Loading…