Methyl chloroformate → [3-(1-Ethyl-5-fluoro-indan-1-yl)-1H-indol-7-yl]-carbamic acid methyl ester

HRID 13713Notes

Reaction equation

HRID 13713 reaction equation
[CH2:1]([C:3]1([C:13]2[C:21]3[C:16](=[C:17]([NH2:22])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].Cl[C:24]([O:26][CH3:27])=[O:25]>N1C=CC=CC=1.CCOCC>[CH3:27][O:26][C:24](=[O:25])[NH:22][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:16]=1[NH:15][CH:14]=[C:13]2[C:3]1([CH2:1][CH3:2])[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 589417073-(1-Ethyl-5-fluoro-indan-1-yl)-1H-indol-7-ylamine

Product 1

HCID 58941708[3-(1-Ethyl-5-fluoro-indan-1-yl)-1H-indol-7-yl]-carbamic acid methyl esterYield 36%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

Dissolve 3-(1-ethyl-5-fluoro-indan-1-yl)-1H-indol-7-ylamine (0.35 g, 1.19 mmol) in pyridine (3 ml). Add methyl chloroformate (0.10 ml, 1.31 mmol, 1.1 equivalents) and stir at room temperature under nitrogen overnight. Dilute with ether, wash with 1N aqueous hydrochloric acid (2×), dry over anhydrous sodium sulfate, filter, and concentrate solution in vacuo. Purify the residue on silica eluting with 0 to 75% ethyl acetate/hexanes over 30 minutes to provide the title compound as a white solid (0.15 g, 36%). LC-MS m/z 353.1 (M++1).

Workup

  1. washwash with 1N aqueous hydrochloric acid (2×)
  2. dry with materialdry over anhydrous sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate solution in vacuo
  5. customPurify the residue on silica eluting with 0 to 75% ethyl acetate/hexanes over 30 minutes

Sources & evidence

ORD record
ord-71866f818b4e40e097b0c842d5917d59
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Reaction notes

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