Methyl 3-phenyl-4-(trifluoromethyl)isothiazole-5-carboxylate → 3-(3-Phenyl-4-(trifluoromethyl)isothiazol-5-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole

HRID 1506512Notes

Reaction equation

HRID 1506512 reaction equation
C1(N2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]3[O:20][N:19]=[C:18]4[C:21]5[C:26]([CH2:27][CH2:28][C:17]=34)=[CH:25][C:24]([CH:29]=[CH2:30])=[CH:23][CH:22]=5)C=N2)C=CC=CC=1.C(C1C=C2C(=CC=1)/C(=N/O)/CCC2)=C.[C:45]1([C:51]2C(C(F)(F)F)=C(C(OC)=O)[S:53][N:52]=2)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>>[C:45]1([C:51]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]3[O:20][N:19]=[C:18]4[C:21]5[C:26]([CH2:27][CH2:28][C:17]=34)=[CH:25][C:24]([CH:29]=[CH2:30])=[CH:23][CH:22]=5)[S:53][N:52]=2)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

4

Reactant 3

HCID 58374139Methyl 3-phenyl-4-(trifluoromethyl)isothiazole-5-carboxylateHCID 671704203-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazoleHCID 121012766(NE)-N-(6-ethenyl-3,4-dihydro-2H-naphthalen-1-ylidene)hydroxylamine2×

Product 1

HCID 671714963-(3-Phenyl-4-(trifluoromethyl)isothiazol-5-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole

Procedure

The titled compound was prepared using the experimental protocol described for Preparation 89A employing 6-vinyl-3,4-dihydronaphthalen-1(2H)-one oxime (Intermediate 1) and methyl 3-phenyl-4-(trifluoromethyl)isothiazole-5-carboxylate (Preparation 103E) as starting materials. The compound had an HPLC retention time=4.25 min. (condition C); LC/MS M+1=424.8.

Sources & evidence

ORD record
ord-9dbb24818afc458f800aaf7964953320
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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