Aluminium lithium hydride → HCID 59160542, compound
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[NH:13][C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[N:28]=3)=[C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[N:23]=[CH:22][CH:21]=[CH:20]4)[N:16]=2)=[CH:7][C:3]=1[C:4](O)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[NH:13][C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[N:28]=3)=[C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[N:23]=[CH:22][CH:21]=[CH:20]4)[N:16]=2)=[CH:7][C:3]=1[CH2:4][OH:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 2-fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)benzoic acid (Example 104) (75 mg, 0.171 mmol) in THF (1 mL) was added LAH (1M solution in THF, 342 uL, 0.342 mmol) and the mixture was stirred at room temperature for 2 hours. The reaction was quenched by addition of ethyl acetate (1 mL) and H2O (3 drops), and the mixture was stirred for 30 min. The mixture was dried over Na2SO4, filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by MPLC (MeOH:CH2Cl2=1:50 (v/v) to 1:20 (v/v)) to afford the title compound (16.9 mg, 23%). (300 MHz, CDCl3) δ 2.50 (3H, s), 4.09 (2H, s), 6.64-6.72 (2H, m), 6.91-6.98 (2H, m), 7.31 (1H, d), 7.39 (1H, t), 8.13 (2H, d), 8.41 (1H, s), 8.84 (2H, dd), MS (ESI) m/z 411 (MH+).