2,6-Lutidine → HCID 89791237, compound

HRID 470589Notes

Reaction equation

HRID 470589 reaction equation
[N:1]([CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]3[N:18]=[C:17]([C:19]4[O:23][N:22]=[C:21]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:20]=4[C:30]([F:33])([F:32])[F:31])[O:16][N:15]=3)[CH:10]=2)[CH:5]1[OH:34])=[N+:2]=[N-:3].N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])(=O)=O>C(Cl)Cl>[N:1]([CH:4]1[CH2:13][CH2:12][C:11]2[CH:10]=[C:9]([C:14]3[N:18]=[C:17]([C:19]4[O:23][N:22]=[C:21]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:20]=4[C:30]([F:33])([F:32])[F:31])[O:16][N:15]=3)[CH:8]=[CH:7][C:6]=2[CH:5]1[O:34][Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 89791392HCID 89791392, compound

Product 1

HCID 89791237HCID 89791237, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Racemic 2-azido-6-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (130 mg, 0.28 mmol) was dissolved in CH2Cl2 (694 μL). To this solution was added 2,6-lutidine (129 μL, 1.1 mmol) and tert-butyldimethylsilyl trifluoromethanesulfonate (133 μL, 0.55 mmol). The reaction was stirred at room temperature for 1 h. After that, the solution was loaded onto a 12 g ISCO column and purified by ISCO Combiflash Companion (0% ethyl acetate-hexane for 3 min then ramp to 20% ethyl acetate-hexane over 5 min then 20% ethyl acetate-hexane for 8 more min, product came out 8-10 min) to afford racemic-3-(6-azido-5-(tert-butyldimethylsilyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl)-5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazole (130 mg, 0.22 mmol, 80%) as a white solid: LCMS=605.34 [M+Na]+.

Workup

  1. custompurified by ISCO Combiflash Companion (0% ethyl acetate-hexane for 3 min
  2. waitthen ramp to 20% ethyl acetate-hexane over 5 min
  3. wait20% ethyl acetate-hexane for 8 more min, product came out 8-10 min

Sources & evidence

ORD record
ord-1a5ed12e2a4e4ed4bb129abb2667833d
Source dataset
uspto-grants-2014_01
Patent number
US08629282B2

Reaction notes

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