Triethylsilane → ethyl 2-(5-cyclopropyl-2-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

HRID 1189541Notes

Reaction equation

[CH:1]1([C:4]2[N:5]([CH2:10][C:11]([O-:13])=[O:12])[C:6]([CH3:9])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH2:14]([SiH](CC)CC)[CH3:15].FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[N:33]1([S:38]([C:41]2[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=2[CH:43]=O)(=[O:40])=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34]1>>[CH:1]1([C:4]2[N:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([CH3:9])=[C:7]([CH2:43][C:42]3[CH:45]=[CH:46][CH:47]=[CH:48][C:41]=3[S:38]([N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)(=[O:40])=[O:39])[CH:8]=2)[CH2:2][CH2:3]1

Participants

Reactant 4

HCID 12052Triethylsilane

HCID 65367Trimethylsilyl triflate

HCID 573845822-(Pyrrolidin-1-ylsulfonyl)benzaldehyde

HCID 866545262-(2-cyclopropyl-5-methyl-1H-pyrrol-1-yl)acetate

Product 1

HCID 58310978ethyl 2-(5-cyclopropyl-2-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetateYield 25%

Procedure

was followed using 2-(2-cyclopropyl-5-methyl-1H-pyrrol-1-yl)acetate (1.25 g, 6.03 mmol), triethylsilane (2.89 mL, 18.1 mmol), trimethylsilyl trifluoromethanesulfonate (2.18 mL, 12.1 mmol) and 2-(pyrrolidin-1-ylsulfonyl)benzaldehyde (1.44 g, 6.03 mmol) to afford ethyl 2-(5-cyclopropyl-2-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (642 mg, 1.49 mmol, 25% yield) as an oil.

Sources & evidence

ORD record: ord-e4cba888f241433383c9921e407f0f63
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674115B2

Reaction notes

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