Aluminium lithium hydride → HCID 59160552, compound

HRID 1958670Notes

Reaction equation

HRID 1958670 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:12][C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)[N:15]=2)=[CH:6][C:3]=1[C:4]#[N:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:12][C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)[N:15]=2)=[CH:6][C:3]=1[CH2:4][NH2:5]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 44545795HCID 44545795, compound

Product 1

HCID 59160552HCID 59160552, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-Fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)benzonitrile (Example 76) (100 mg, 0.238 mmol) in THF (1.5 mL) was added LAH (1M solution in THF, 476 uL, 0.476 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 (53.2 mg, 53%). (300 MHz, CDCl3+CD3OD) δ 2.49 (3H, s), 3.87 (2H, s), 4.17 (2H, s), 6.95-7.01 (2H, m), 7.17-7.33 (3H, m), 7.35-7.43 (2H, m), 7.96 (1H, d), 8.08-8.17 (3H, m), 8.91 (1H, dd), 10.40 (1H, bs), MS (ESI) m/z 424 (MH+).

Workup

  1. customThe reaction was quenched by addition of ethyl acetate (1 mL) and H2O (3 drops)
  2. stirringthe mixture was stirred for 30 min
  3. dry with materialThe mixture was dried over Na2SO4
  4. filtrationfiltered through celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by MPLC (MeOH:CH2Cl2=1:50 (v/v) to 1:20 (v/v))

Sources & evidence

ORD record
ord-d1c4bd1f8032406485dddedaac9569f2
Source dataset
uspto-grants-2013_04
Patent number
US08410146B2

Reaction notes

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