Triethylsilane → HCID 53245778, compound

HRID 1189545Notes

Reaction equation

HRID 1189545 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:9]([CH2:14][C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[C:10]([CH3:13])=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.C([SiH](CC)CC)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[C:44]1([S:50]([C:53]2[CH:60]=[CH:59][CH:58]=[CH:57][C:54]=2[CH:55]=O)(=[O:52])=[O:51])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:9]([CH2:14][C:15]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:16])[C:10]([CH3:13])=[C:11]([CH2:55][C:54]3[CH:57]=[CH:58][CH:59]=[CH:60][C:53]=3[S:50]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)(=[O:52])=[O:51])[CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 6409162-(phenylsulfonyl)benzaldehydeHCID 86654527HCID 86654527, compound

Product 1

HCID 53245778HCID 53245778, compoundYield 17%

Procedure

was followed using benzyl 2-(2-(2-chloropyridin-4-yl)-5-methyl-1H-pyrrol-1-yl)acetate (0.900 g, 2.64 mmol), triethylsilane (1.27 ml, 7.92 mmol), trimethylsilyl trifluoromethanesulfonate (0.954 ml, 5.28 mmol) and 2-(phenylsulfonyl)benzaldehyde (0.650 g, 2.64 mmol) to afford benzyl 2-(5-(2-chloropyridin-4-yl)-2-methyl-3-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (514 mg, 0.450 mmol, 17% yield). 1D-NOESY experiment was performed to confirm the drawn regioisomer (irradiation of methyl group and 1-2% interaction with both methylene groups).

Sources & evidence

ORD record
ord-e615438cb55b4f2cafac992a52e9e1c8
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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