Aluminium lithium hydride → HCID 58303926, compound

HRID 1404121Notes

Reaction equation

HRID 1404121 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][C:12]1[C:13]([O:30][CH3:31])=[C:14]2[C:18](=[C:19]([F:21])[CH:20]=1)[N:17]([CH2:22][CH3:23])[CH:16]=[C:15]2[CH2:24][C:25]([N:27]([CH3:29])[CH3:28])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][C:12]1[C:13]([O:30][CH3:31])=[C:14]2[C:18](=[C:19]([F:21])[CH:20]=1)[N:17]([CH2:22][CH3:23])[CH:16]=[C:15]2[CH2:24][CH2:25][N:27]([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58303937HCID 58303937, compound

Product 1

HCID 58303926HCID 58303926, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 29-3 (100 mg, 0.24 mmol) in THF (10 mL) was added lithium aluminum hydride (19 mg, 0.48 mmol). The mixture was stirred at room temperature overnight. Na2SO4.10H2O was added and the reaction mixture was filtered and the filtrate was evaporated to give the crude product which was purified by preparative HPLC (basic condition, water/CH3CN, 43-53% CH3CN in 7.5 min, RT=7.3 min) to afford 29-4 (22 mg, 23%) as a yellow solid. 1H-NMR (400 MHz, CDCl3): δ (ppm) 7.52-7.50 (br.s, 2H), 7.20-7.16 (m, 2H), 6.76 (s, 1H), 6.66 (d, J=12.8 Hz, 1H), 3.96 (q, J=7.2 Hz, 2H), 3.81 (s, 3H), 3.14 (t, J=7.2 Hz, 2H), 3.06-2.98 (m, 4H), 2.69 (t, J=7.6 Hz, 2H), 2.38 (s, 6H) 1.30 (t, J=7.2 Hz, 3H). LRMS: calc 408.5 and found: 409.2 [M+1].

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customto give the crude product which
  4. customwas purified by preparative HPLC (basic condition, water/CH3CN, 43-53% CH3CN in 7.5 min, RT=7.3 min)

Sources & evidence

ORD record
ord-5987c243c50e4e7b8acd6ff7583c702e
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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