Aluminium lithium hydride → HCID 59160542, compound

HRID 1958671Notes

Reaction equation

HRID 1958671 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

HCID 21226445Aluminium lithium hydrideHCID 59160544HCID 59160544, compound

Product 1

HCID 59160542HCID 59160542, compoundYield 23.3%

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)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+).

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-fbb21a5dbb544a4a9fc53ad02db80974
Source dataset
uspto-grants-2013_04
Patent number
US08410146B2

Reaction notes

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