Iodoethane → HCID 11521901, compound

HRID 907125Notes

Reaction equation

HRID 907125 reaction equation
[H-].[Na+].NC1NC2C(C=1C#N)=CC=C([N+]([O-])=[O:16])C=2.I[CH2:19][CH3:20].[NH2:21][C:22]1[N:23]([CH2:36][CH3:37])[C:24]2[C:29]([C:30]=1[C:31]#[N:32])=[CH:28][CH:27]=[C:26]([N+:33]([O-:35])=[O:34])[CH:25]=2>CCCCCC.CS(C)=O.CCOC(C)=O>[C:31]([C:30]1[C:29]2[C:24](=[CH:25][C:26]([N+:33]([O-:35])=[O:34])=[CH:27][CH:28]=2)[N:23]([CH2:36][CH3:37])[C:22]=1[NH:21][C:19](=[O:16])[CH3:20])#[N:32]

Participants

8

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 163613672-Amino-6-nitro-1H-indole-3-carbonitrileHCID 59425037HCID 59425037, compound

Product 1

HCID 11521901HCID 11521901, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (42 mg, 1.05 mmol, 60% w/w suspension in mineral oil) was washed with hexane and taken up in dimethylsulfoxide (1 mL). A solution of 2-amino-6-nitro-1H-indole-3-carbonitrile, prepared in procedure 1T) in dimethylsulfoxide (1 mL) was added by syringe, and the resulting mixture was stirred for 20 min. Then, iodoethane (77 μL, 0.96 mmol) was added by syringe, and the mixture was stirred for 14 h. The reaction was then poured into EtOAc (50 mL), and this solution was washed with water (3×50 mL) and saturated brine (40 mL). The aqueous phases were back-extracted with EtOAc, and the organic extracts were combined, dried over Na2SO4, filtered and evaporated. The residual material was separated by column chromatography over silica gel (EtOAc/hexanes, 1/1) to afford first a small amount of a dialkylated analog, then the desired compound, 2-amino-1-ethyl-6-nitro-1H-indole-3-carbonitrile (114 mg, 52%), and finally unreacted starting material. The desired product was isolated as an orange powder.

Workup

  1. additionwas added by syringe
  2. stirringthe mixture was stirred for 14 h
  3. washthis solution was washed with water (3×50 mL) and saturated brine (40 mL)
  4. extractionThe aqueous phases were back-extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residual material was separated by column chromatography over silica gel (EtOAc/hexanes, 1/1)
  9. customto afford first a small amount of a dialkylated analog

Sources & evidence

ORD record
ord-806e8180ef8942919525f89b6a9d69d9
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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