Propyl chloroformate → HCID 11653183, compound

HRID 907130Notes

Reaction equation

HRID 907130 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:19]#[N:20])=[CH:7][N:8]2[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.Cl[C:22]([O:24][CH2:25][CH2:26][CH3:27])=[O:23].C(N(CC)CC)C>CCO>[CH2:25]([O:24][C:22](=[O:23])[NH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:19]#[N:20])=[CH:7][N:8]2[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1)[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 7998Propyl chloroformateHCID 8471TriethylamineHCID 59426071HCID 59426071, compound

Product 1

HCID 11653183HCID 11653183, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Amino-1-(4-methoxyphenyl)-1H-indole-3-carbonitrile (30 mg, 0.12 mmol), was suspended in EtOH (300 μL). Propyl chloroformate (168 μL, 1.5 mmol) was added, and this mixture was stirred at room temperature overnight. The addition of triethylamine (300 μL), followed by another hour of stirring at room temperature, completed the reaction. This reaction mixture was loaded directly onto a silica column, and was eluted with CH2Cl2. Another silica column (3/2, ether/hexanes) was needed to fully purify the product, [3-cyano-1-(4-methoxy-phenyl)-1H-indol-6-yl]-carbamic acid propyl ester (19 mg, 45%), as a white solid.

Workup

  1. waitfollowed by another hour
  2. stirringof stirring at room temperature
  3. customthe reaction
  4. washwas eluted with CH2Cl2
  5. customto fully purify the product, [3-cyano-1-(4-methoxy-phenyl)-1H-indol-6-yl]-carbamic acid propyl ester (19 mg, 45%)

Sources & evidence

ORD record
ord-955bb78db53343448bbeabb07f907ec6
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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