Ammonia → 5-Fluoro-1H-indole-2-carbaldehyde

HRID 511847Notes

Reaction equation

HRID 511847 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17](N(OC)C)=[O:18])=[CH:11]2.N.ClCCl>O1CCCC1>[F:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH:17]=[O:18])=[CH:11]2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 21226445Aluminium lithium hydride2×HCID 23003585HCID 23003585, compound

Product 1

HCID 189681295-Fluoro-1H-indole-2-carbaldehydeYield 103.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminium hydride (0.094 g, 2.488 mmol) was added to a solution of 5-fluoro-N-methoxy-N-methyl-1H-indole-2-carboxamide (0.691 g, 3.11 mmol) in tetrahydrofuran (10 ml) at 0° C. and stirred for 1 hour. The reaction mixture was cooled to 0° C. and 25% ammonia solution was added dropwise to the reaction mixture until lithium aluminium hydride color turn gray to white. Then dichloromethane and cerite was added to the reaction mixture and stirred for 30 min. The mixture was filtered through a pad of Celite and concentrated in vacuo to give 523 mg of the crude title compound. This was used for the next step without further purification:

Workup

  1. stirringstirred for 30 min
  2. filtrationThe mixture was filtered through a pad of Celite
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2eadf4a68a4405fa071d8c2e3afd00b
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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