Triethylsilane → HCID 57435078, compound

HRID 1366889Notes

Reaction equation

HRID 1366889 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)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=1)=[O:11]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 1489203HCID 1489203, compound

Product 1

HCID 57435078HCID 57435078, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (0.323 mL, 2.03 mmol) was added to a stirring, room temperature solution of methyl-4-phenylacetyl-1H-pyrrole-2-carboxylate (0.1593 g, 0.655 mmol) in trifluoroacetic acid (TFA) (1.47 mL, 0.45 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 27 (0.0755 g, 50.3%): 1H (CDCl3, 400 MHz): δ 9.17 (1H, broad s), 7.32-7.25 (2H, m), 7.23-7.17 (3H, m), 6.80 (1H, s), 6.69 (1H, s), 3.85 (3H, s), 2.93-2.85 (2H, m), 2.84-2.75 (2H, m) ppm. 13C (CDCl3, 100 MHz): δ 161.97, 142.15, 128.70, 128.55, 126.13, 125.96, 122.40, 121.26, 115.28, 51.67, 37.57, 28.92 ppm. DEPT (CDCl3, 100 MHz): CH3 carbons: 51.67; CH2 carbons: 37.57, 28.92; CH carbons: 128.70, 128.55, 126.13, 121.26, 115.28 ppm. HPLC: 10.033 min. (Starting material: 8.751 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-f9220ea570bb4cd8bd2d25f28e1f67b8
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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