Trifluoroacetic anhydride → Methyl 7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylate

HRID 872190Notes

Reaction equation

HRID 872190 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:7][NH:8][CH:9]=1)=[O:4].C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C(O)(C(F)(F)F)=O>[O:15]=[C:13]1[C:7]2[NH:8][CH:9]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:6]=2[CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 682765264-[4-(methoxycarbonyl)-1H-pyrrol-3-yl]butanoic acid

Product 1

HCID 68276513Methyl 7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylateYield 70.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-[4-(methoxycarbonyl)-1H-pyrrol-3-yl]butanoic acid (500 mg, 2.36 mmol) was dissolved in TFA (3 mL). TFAA (0.329 mL, 2.36 mmol) was added and the reaction was stirred at room temperature for 1 h. Organic solvent was evaporated to dryness and the residue suspended in Et2O (15 mL) and filtrated to give 320 mg (yield: 64%) of the title compound as a light yellow solid.

Workup

  1. customOrganic solvent was evaporated to dryness
  2. filtrationfiltrated

Sources & evidence

ORD record
ord-b1ff4532afac4fb2a492ee8c8b9c5a00
Source dataset
uspto-grants-2015_03
Patent number
US08975267B2

Reaction notes

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