Aluminium lithium hydride → HCID 178436720, compound

HRID 1192530Notes

Reaction equation

HRID 1192530 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:24](N(OC)C)=[O:25])[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)=[C:6](/[N:10]=[N:11]/[N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[C:7]=1[C:8]#[CH:9].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[O:25])[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)=[C:6](/[N:10]=[N:11]/[N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[C:7]=1[C:8]#[CH:9]

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178436722HCID 178436722, compound

Product 1

HCID 178436720HCID 178436720, compoundYield 47%

Conditions

Temperature
-78 °C

Procedure

A solution of 4-chloro-6-[(1E)-3,3-diethyltriaz-1-en-1-yl]-5-ethynyl-3′-fluoro-N-methoxy-N-methylbiphenyl-2-carboxamide (0.50 g, 1.2 mmol) in tetrahydroduran (5 mL) at −78° C. was treated with 1.0 M lithium aluminum hydride in tetrahydroduran (2.5 mL, 2.5 mmol) dropwise and stirred at −78° C. for 2 hours. The reaction mixture was quenched with water (0.5 mL) at −78° C., diluted with ethyl acetate (50 mL), and warmed to 20° C. The organic layer was separated, washed with 1 M HCl (30 mL), water and brine, dried with sodium sulfate, filtered, and concentrated to a crude residue. Purification by flash column chromatography using ethyl acetate in hexanes (0%-20%) gave the desired product (0.20 g, 47%). LCMS for C19H18ClFN3O (M+H)+: m/z=358.1; Found: 357.9.

Workup

  1. customThe reaction mixture was quenched with water (0.5 mL) at −78° C.
  2. additiondiluted with ethyl acetate (50 mL)
  3. temperaturewarmed to 20° C
  4. customThe organic layer was separated
  5. washwashed with 1 M HCl (30 mL), water and brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a crude residue
  9. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-bde9d2799f674b84a63c5a26089600ca
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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