Tetrahydrofuran → 4-((3-ethylphenyl)(5-phenyl-2-trityl-2H-1,2,4-triazol-3-yl)methylamino)benzonitrile
Reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].[C:6]1([C:12]2[N:16]=[CH:15][N:14]([C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(C1C=[C:40]([CH:51]=[CH:52]C=1)/[CH:41]=[N:42]/[C:43]1[CH:50]=[CH:49][C:46]([C:47]#[N:48])=[CH:45][CH:44]=1)C.[Cl-].[NH4+].[CH2:56]1COCC1>>[CH2:4]([C:3]1[CH:2]=[C:41]([N:42]([CH2:56][C:15]2[N:14]([C:17]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:13]=[C:12]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:16]=2)[C:43]2[CH:44]=[CH:45][C:46]([C:47]#[N:48])=[CH:49][CH:50]=2)[CH:40]=[CH:51][CH:52]=1)[CH3:5]Participants
6
Procedure
BuLi (0.295 mL, 1.6 M in hexanes, 0.47 mmol) was added dropwise to a solution of 3-phenyl-1-trityl-1H-1,2,4-triazole (182 mg, 0.47 mmol) in THF (4 mL) at −78° C. The mixture was stirred for 10 min. A solution of Intermediate 380.1 (100 mg, 0.43 mmol) in THF (0.7 mL) was added dropwise. The mixture was warmed to ambient temperature over 1 h. Ammonium chloride (50 mg) was added and the mixture was concentrated. Purification by flash chromatrography afforded 215 mg of Intermediate 380.2. 1H NMR (400 MHz, CDCl3) δ ppm 1.18 (t, J=7.58 Hz, 3H) 2.52 (q, J=7.74 Hz, 2H) 5.09 (d, J=9.05 Hz, 1H) 6.93 (d, J=7.34 Hz, 1H) 6.98-7.10 (m, 1H) 7.11-7.20 (m, 3H) 7.20-7.27 (m, 8H) 7.33-7.48 (m, 12H) 8.06-8.18 (m, 3H).
Workup
- concentrationthe mixture was concentrated
- customPurification by flash chromatrography
Sources & evidence
- ORD record
- ord-d5e9c806f6584cada9e5bc553f9277e3
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576098B2
Reaction notes
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