Indole → HCID 9904878, compound

HRID 1601038Notes

Reaction equation

HRID 1601038 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Cl.[C:13]([C:15]1[CH:28]=[CH:27][C:18]([CH2:19][N:20]2[C:24]([CH2:25]Cl)=[CH:23][N:22]=[CH:21]2)=[CH:17][CH:16]=1)#[N:14].O>CN(C=O)C.C(Cl)(Cl)Cl.CCOCC.CO>[C:13]([C:15]1[CH:16]=[CH:17][C:18]([CH2:19][N:20]2[C:24]([CH2:25][N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:3]=[CH:2]3)=[CH:23][N:22]=[CH:21]2)=[CH:27][CH:28]=1)#[N:14]

Participants

9

Reactant 4

HCID 798IndoleHCID 962WaterHCID 24758Sodium hydrideHCID 97953574-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochloride

Product 1

HCID 9904878HCID 9904878, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Indole (117 mg, 1.0 mmol) dissolved in DMF (15 mL) was treated with NaH (48 mg, 2 mmol) and stirred for 30 minutes before the addition of the chloride from Step 1 (268 mg, 1 mmol). The mixture was stirred for 16 h, poured into water, extracted with EtOAc (3×), washed with aqueous NaHCO3 then brine, dried and evaporated to give an oil. Chromatography of this oil (silica gel; 2.5% MeOH in CHCl3) gave an oil which solidified when stirred in ether. Filtration afforded the title product as an off-white solid.

Workup

  1. extractionextracted with EtOAc (3×)
  2. washwashed with aqueous NaHCO3
  3. dry with materialbrine, dried
  4. customevaporated
  5. customto give an oil
  6. filtrationFiltration

Sources & evidence

ORD record
ord-3cdb31d3ee654a39b209bba7c23a0ad8
Source dataset
uspto-grants-1999_11
Patent number
US05977134

Reaction notes

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