Lithium aluminum hydride → HCID 58565373, compound

HRID 2175315Notes

Reaction equation

HRID 2175315 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:18](OCC)=[O:19])[N:8]2[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:4][CH:3]=1.[AlH4-].[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:18][OH:19])[N:8]2[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 58565337HCID 58565337, compound

Product 1

HCID 58565373HCID 58565373, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 6-chloro-1-(3-fluorophenyl)-1H-indole-2-carboxylate (0.60 g, 1.9 mmol) in tetrahydrofuran (10 mL) was cooled at −78° C. Lithium tetrahydroaluminate (1 M) in tetrahydrofuran (6.0 mL, 6.0 mmol) was added dropwise and the resulting mixture was stirred at this temperature for 1 hour. The reaction was quenched by the addition of water (0.12 mL) and stirred for 10 minutes, warmed up to room temperature, followed by the addition of 5% aqueous NaOH solution (0.12 mL) with stirring for 10 minutes. Then additional water (0.36 mL) was added and stirring was continued for 10 minutes. The mixture was filtered, dried over MgSO4 and concentrated to give the crude product (0.53 g). The residue was used in the next step directly. LCMS calculated for C15H12ClFNO(M+H)+: m/z=276.1. Found: 276.0.

Workup

  1. customThe reaction was quenched by the addition of water (0.12 mL)
  2. stirringstirred for 10 minutes
  3. additionfollowed by the addition of 5% aqueous NaOH solution (0.12 mL)
  4. stirringwith stirring for 10 minutes
  5. additionThen additional water (0.36 mL) was added
  6. stirringstirring
  7. waitwas continued for 10 minutes
  8. filtrationThe mixture was filtered
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d09094a86b5f4312b9f9ed5cd9841125
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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