Lawesson's reagent → 5-(7-Bromo-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole
Reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[Br:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:30](=O)[CH:29]([NH:35][C:36]([C:38]1[O:42][N:41]=[C:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:39]=1[C:49]([F:52])([F:51])[F:50])=O)[CH2:28][CH2:27]2>C1(C)C=CC=CC=1>[Br:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:30]1[S:10][C:36]([C:38]3[O:42][N:41]=[C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:39]=3[C:49]([F:52])([F:51])[F:50])=[N:35][C:29]=1[CH2:28][CH2:27]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
To Lawesson's Reagent (1.393 g, 3.44 mmol) was added N-(6-bromo-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxamide (Preparation 82C, 1.1 g, 2.295 mmol) followed by toluene (10 mL). The reaction mixture was heated at 140° C. behind a safety shield for 15 h. The reaction mixture was cooled to room temperature, loaded onto a silica gel column (with toluene) and purified using hexane/EtOAc (9.25:0.75, 600 mL). The desired fractions were collected and concentrated to yield a pale yellow solid. The solid was triturated with acetonitrile (20 mL), filtered and washed with acetonitrile (2×5 mL) to yield 5-(7-bromo-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole (0.935 g, 1.959 mmol, 85% yield) as a pale yellow solid. LC/MS M+1=478.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- custompurified
- customThe desired fractions were collected
- concentrationconcentrated
- customto yield a pale yellow solid
- customThe solid was triturated with acetonitrile (20 mL)
- filtrationfiltered
- washwashed with acetonitrile (2×5 mL)
Sources & evidence
- ORD record
- ord-c09e4eadd71a45e2b6dd9964c5c1c1bf
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216972B2
Reaction notes
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