Sodium Carbonate → tert-Butyl [(1-{[3-(methylsulfonyl)phenyl]sulfonyl}-5-(3-pyridyl)-1H-pyrrol-3-yl)methyl]methylcarbamate

HRID 554367Notes

Reaction equation

HRID 554367 reaction equation
Br[C:2]1[N:6]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:11]=2)(=[O:9])=[O:8])[CH:5]=[C:4]([CH2:20][N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:3]=1.[N:30]1[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][S:16]([C:12]1[CH:11]=[C:10]([S:7]([N:6]2[C:2]([C:32]3[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=3)=[CH:3][C:4]([CH2:20][N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:5]2)(=[O:9])=[O:8])[CH:15]=[CH:14][CH:13]=1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 66924810tert-butyl [(5-bromo-1-{[3-(methylsulfonyl)phenyl]sulfonyl}-1H-pyrrol-3-yl)methyl]methylcarbamate

Product 1

HCID 66925104tert-Butyl [(1-{[3-(methylsulfonyl)phenyl]sulfonyl}-5-(3-pyridyl)-1H-pyrrol-3-yl)methyl]methylcarbamateYield 67%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Using tert-butyl [(5-bromo-1-{[3-(methylsulfonyl)phenyl]sulfonyl}-1H-pyrrol-3-yl)methyl]methylcarbamate (459 mg), 3-pyridineboronic acid (222 mg), sodium carbonate (287 mg) and tetrakis(triphenylphosphine)palladium (53.1 mg), a procedure as in Reference Example 267 was performed to give the title compound as a white solid (yield 305 mg, 67%).

Sources & evidence

ORD record
ord-331d416b42354c5480fcf55d4a85d94f
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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