Tetrabutylammonium Fluoride → N-[(5)-(5-bromopyridin-2-yl)(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-2-(4-isopropylphenyl)acetamide
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([C:22]2[N:23]=[N:24][N:25]([CH2:27][Si](C)(C)C)[CH:26]=2)[NH:9][C:10](=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[N:6][CH:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([C:22]2[N:23]=[N:24][N:25]([CH3:27])[CH:26]=2)[NH:9][C:10](=[O:21])[CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:17]=2)=[N:6][CH:7]=1Participants
Procedure
To a solution of N-((S)-(5-bromopyridin-2-yl){1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)-2-(4-isopropylphenyl)acetamide (0.4 g, 0.80 mmol) in THF (5.0 mL) was added a solution of TBAF in THF (0.84 mL, 1 M). The reaction was stirred at room temperature for 1 h. The solvent was removed and the residue was purified by silica flash chromatography (gradient, 10-100% EtOAc in hexanes) to give N-[(S)-(5-bromopyridin-2-yl) (1-methyl-1H-1,2,3-triazol-4-yl)methyl]-2-(4-isopropylphenyl)acetamide (0.22 g, 65%). ES-MS [M+1]+: 428.0. 1H NMR (CDCl3, 400 MHz) δ 8.53 (d, J=2.0 Hz, 1H), 7.76 (dd, J=2.4, 8.0 Hz, 1H), 7.4w (s, 1H), 7.36 (d, J=6.8 Hz, 1H), 7.23 (d, J=8.0 Hz, 1H), 7.22 (s, 4H), 6.26 (d, J=6.8 Hz, 1H), 4.01 (s, 3H), 3.62 (s, 2H), 2.94-2.85 (m, J=6.8 Hz, 1H), 1.25 (d, J=7.2 Hz, 6H). HRMS (ES) [M+1]+ calcd for C20H22BrN5O: 428.1081. Found: 428.1112.
Workup
- customThe solvent was removed
- customthe residue was purified by silica flash chromatography (gradient, 10-100% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-f3cc3a7dc8a94d18a8f7bc97c60a397e
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987310B2
Reaction notes
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