Trifluoroacetic acid → methyl 3-phenyl-1H-indole-6-carboxylate

HRID 409908Notes

Reaction equation

HRID 409908 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9](C(OC(C)(C)C)=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596260441-tert-Butyl 6-methyl 3-phenyl-1H-indole-1,6-dicarboxylate

Product 1

HCID 24939030methyl 3-phenyl-1H-indole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butyl 6-methyl 3-phenyl-1H-indole-1,6-dicarboxylate 16a (4.04 mmol, 1.42 g) in CH2Cl2 (8 mL) was added 6 mL of TFA. The resulting solution was stirred for 3 h. The mixture was then concentrated and washed with hexanes to afford 16b.

Workup

  1. concentrationThe mixture was then concentrated
  2. washwashed with hexanes

Sources & evidence

ORD record
ord-3a18deb899014b6ab34f6eec018d0cf9
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

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