Triethylsilane → HCID 57435077, compound

HRID 1724742Notes

Reaction equation

HRID 1724742 reaction equation
C([SiH](CC)CC)C.[CH3:8][O:9][C:10]([C:12]1[NH:13][CH:14]=[C:15]([C:17](=O)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=1)=[O:11]>FC(F)(F)C(O)=O>[CH3:8][O:9][C:10]([C:12]1[NH:13][CH:14]=[C:15]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=1)=[O:11]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 2764013Methyl 4-benzoyl-1H-pyrrole-2-carboxylate

Product 1

HCID 57435077HCID 57435077, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (0.215 mL, 1.35 mmol) was added to a stirring, room temperature solution of methyl-4-benzoyl-1H-pyrrole-2-carboxylate (0.1118 g, 0.488 mmol) in trifluoroacetic acid (TFA) (1.04 mL, 0.47 M) under N2. After stirring overnight, the reaction was complete by HPLC. The TFA was removed under vacuum, and the crude product was taken up in EtOAc, washed with brine, dried with Na2SO4, filtered, concentrated, and purified by silica gel chromatography (Combiflash column, 95:5 Hexanes: EtOAc) to obtain pure 25 (0.0604 g, 57.5%): 1H (CDCl3, 400 MHz): δ 9.44 (11H, broad s), 7.34-7.21 (5H, m), 6.78 (1H, s), 6.75 (1H, s), 3.853 (2H, s), 3.846 (3H, s) ppm. 13C (CDCl3, 100 MHz): δ 162.09, 141.68, 128.85, 128.70, 126.25, 125.55, 122.67, 121.86, 115.74, 51.70, 33.41 ppm. HPLC: 9.693 min. (Starting material: 8.611 min.)

Workup

  1. customThe TFA was removed under vacuum
  2. washwashed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (Combiflash column, 95:5 Hexanes: EtOAc)

Sources & evidence

ORD record
ord-bd304aef12a249e4877d2955ca9dd692
Source dataset
uspto-grants-2009_02
Patent number
US07488747B2

Reaction notes

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