Propyl chloroformate → HCID 11653183, compound

HRID 502149Notes

Reaction equation

HRID 502149 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), is suspended in EtOH (300 μL). Propyl chloroformate (168 μL, 1.5 mmol) is added, and this mixture is stirred at room temperature overnight. The addition of triethylamine (300 μL), followed by another hour of stirring at room temperature, completes the reaction. This reaction mixture is loaded directly onto a silica column, and is eluted with CH2Cl2. Another silica column (3/2, ether/hexanes) is 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. washis 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-51b98c6f5a4a4720a6b003c822e8762f
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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