Aluminium lithium hydride → HCID 22638805, compound

HRID 2416263Notes

Reaction equation

HRID 2416263 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CON(C)[C:10]([CH:12]1[CH2:14][CH:13]1[CH2:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[C:25]#[N:26])=[O:11]>O1CCCC1>[CH:10]([CH:12]1[CH2:14][CH:13]1[CH2:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[C:25]#[N:26])=[O:11]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 86587685HCID 86587685, compound

Product 1

HCID 22638805HCID 22638805, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of lithium aluminum hydride (0.020 g, 0.53 mmol) in anhydrous tetrahydrofuran (5 ml) at −45° C. was treated with a solution 2-(3-cyano-1H-indol-5-ylmethyl)-cyclopropanecarboxylic acid methoxy-methyl-amide in 5 ml tetrahydrofuran. After 30 min at −45° C. an additional 0.53 mmol lithium aluminum hydride was added. The reaction was quenched with water followed by 1 N sodium hydroxide after another 30 min. The aluminum salts were removed by filtration and the filtrate was concentrated in vacuo to afford 5-(2-Formyl-cyclopropylmethyl)-1H-indole-3-carbonitrile (0.034 g, 57%) as a light yellow film. 1H-NMR (400 MHz, CDCl3) 9.07 (1H, d, J=5.16 Hz), 7.71 (1H, s), 7.58 (1H, s), 7.39 (1H, d, J=8.2 Hz), 7.22 (1H, m), 6.98 (1H, s), 2.80 (2H, m), 1.86 (2H), 1.40 (1H, m), 1.11 (1H, m).

Workup

  1. customThe reaction was quenched with water
  2. customThe aluminum salts were removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f2275d518867476e8a90dc4614edf9ab
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

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