Triethylsilane → 4-[2-(4-Chloro-phenyl)-ethyl]-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 1434791Notes

Reaction equation

HRID 1434791 reaction equation
C([SiH](CC)CC)C.[CH2:8]([O:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([C:19](=O)[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C:17]=1[CH3:18])=[O:12])[CH3:9]>FC(F)(F)C(O)=O>[CH2:8]([O:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C:17]=1[CH3:18])=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 574351104-[2-(4-Chloro-phenyl)-acetyl]-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

Product 1

HCID 575617544-[2-(4-Chloro-phenyl)-ethyl]-3-methyl-1H-pyrrole-2-carboxylic acid ethyl esterYield 46%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (3 equivalents) was added to a solution of 85 in trifluoroacetic acid (2 mL per mmol). The mixture was stirred for 48 h at room temperature. The TFA was removed under vacuum and the crude product was taken up in AcOEt, washed with NaOH (2 M), brine, dried with Na2SO4, filtered and concentrated to give crude product. The residue was purified by HPLC. Yield: 46% for two steps. 1H-NMR (400 MHz, CDCl3): δ 1.35 (t, 3H), 2.26 (s, 3H), 2.69 (m, 2H), 2.78 (m, 2H), 4.31 (q, 2H), 6.55 (d, 1H), 7.08 (d, 2H), 7.22 (d, 2H), 8.86 (s broad, 1H) ppm.

Workup

  1. customThe TFA was removed under vacuum
  2. washwashed with NaOH (2 M), brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product
  7. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-6aca8b4fb62c4494aa0fa6518a0c0669
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

Loading…