Trifluoroacetic acid → 4-Amino-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29301Notes

Reaction equation

HRID 29301 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16]C(OC(C)(C)C)=O)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].FC(F)(F)C(O)=O>ClCCCl>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 687118484-Tert-butoxycarbonylamino-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687122774-Amino-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To 4-tert-butoxycarbonylamino-3-methyl-benzofuran-2-carboxylic acid ethyl ester (624 mg, 1.95 mmol, prepared according to Example 59, Step 1) was added 1,2-dichloroethane (12 mL) and trifluoroacetic acid (TFA, 6 mL). The reaction was stirred at room temperature for 2 hours. Solvent was removed in vacuo to provide 4-amino-3-methyl-benzofuran-2-carboxylic acid ethyl ester in quantitative yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.3 (t, J=7.1 Hz, 3 H) 2.7 (s, 3 H) 4.3 (q, J=7.1 Hz, 2 H) 6.5 (dd, J=7.8, 0.8 Hz, 1 H) 6.8 (d, J=8.3 Hz, 1 H) 7.2 (t, J=8.1 Hz, 1 H).

Workup

  1. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-2070c549590c4ebda1f82cffb50aea63
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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