Trifluoroacetic acid → HCID 59030420, compound

HRID 502278Notes

Reaction equation

HRID 502278 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[C:9]1[C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])=[CH:21][CH:20]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:29]([O:28][C:26](=[O:27])[NH:25][C:22]1[CH:21]=[CH:20][C:19]([C:9]2[NH:8][C:16]3[C:11]([CH:10]=2)=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=3)=[CH:24][CH:23]=1)([CH3:31])[CH3:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 49772678HCID 49772678, compound

Product 1

HCID 59030420HCID 59030420, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(4-Isopropoxycarbonylamino-phenyl)-6-methoxy-indole-1-carboxylic acid tert-butyl ester (17.4 g, 41 mmol), CH2Cl2 (50 mL), and TFA (50 mL) was stirred at room temperature for 1 h. The reaction mixture was concentrated, diluted in CH2Cl2, and washed with sat. aq. NaHCO3. The organic layer was dried, concentrated, and triturated with ether to provide [4-(6-methoxy-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester (11.4 g, 86%) as a grayish solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted in CH2Cl2
  3. washwashed with sat. aq. NaHCO3
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customtriturated with ether

Sources & evidence

ORD record
ord-37d4c229e5b94b339e8aeb8284dbe811
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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