Iodoethane → HCID 11521901, compound

HRID 502144Notes

Reaction equation

HRID 502144 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) is 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) is added by syringe, and the resulting mixture is stirred for 20 min. Then, iodoethane (77 μL, 0.96 mmol) is added by syringe, and the mixture is stirred for 14 h. The reaction is then poured into EtOAc (50 mL), and this solution is washed with water (3×50 mL) and saturated brine (40 mL). The aqueous phases are back-extracted with EtOAc, and the organic extracts are combined, dried over Na2SO4, filtered and evaporated. The residual material is 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 is isolated as an orange powder.

Workup

  1. additionis added by syringe
  2. stirringthe mixture is stirred for 14 h
  3. washthis solution is washed with water (3×50 mL) and saturated brine (40 mL)
  4. extractionThe aqueous phases are back-extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residual material is 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-c910c84ea7c74e18ab2a0f2d06ca1a9c
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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