Water → HCID 9861466, compound

HRID 1245014Notes

Reaction equation

HRID 1245014 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][C:6]1[C:7]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[NH:9][CH:10]=1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>O1CCCC1>[NH2:2][CH2:1][CH2:3][CH2:4][CH2:5][C:6]1[C:7]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[C:8]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[NH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21922602HCID 21922602, compound

Product 1

HCID 9861466HCID 9861466, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.94 g (3.08 mmol) of 4-(3-cyanopropyl)-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole [prepared as described in step 67(i) above] in 50 ml of tetrahydrofuran was added dropwise to a suspension of 468 mg (12.32 mmol) of lithium aluminum hydride in 100 ml of tetrahydrofuran at room temperature with stirring. The resulting mixture was stirred at 60° C. for 3 hours. After cooling to room temperature, 0.47 ml of a 15% aqueous solution of sodium hydroxide and 20 ml of water were successively added gradually to the reaction mixture. The resulting mixture was filtered and the filtrate thus obtained was concentrated by evaporation under reduced pressure. The resulting residue was purified by chromatography on a silica gel column using a 25:1 by volume mixture of ethyl acetate and isopropylamine as the eluant to give 410 mg (yield 43%) of the title compound as a pale red powder.

Workup

  1. stirringThe resulting mixture was stirred at 60° C. for 3 hours
  2. filtrationThe resulting mixture was filtered
  3. customthe filtrate thus obtained
  4. concentrationwas concentrated by evaporation under reduced pressure
  5. customThe resulting residue was purified by chromatography on a silica gel column
  6. additionby volume mixture of ethyl acetate and isopropylamine as the eluant

Sources & evidence

ORD record
ord-5a68c83984da4087839e42871ea1a44d
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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