Sodium Carbonate → HCID 66925065, compound

HRID 554365Notes

Reaction equation

HRID 554365 reaction equation
Br[C:2]1[N:6]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]#[N:17])(=[O:9])=[O:8])[CH:5]=[C:4]([CH2:18][N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:3]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=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>[C:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[S:7]([N:6]1[C:2]([C:30]2[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=2)=[CH:3][C:4]([CH2:18][N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:5]1)(=[O:9])=[O:8])#[N:17]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 66924849HCID 66924849, compound

Product 1

HCID 66925065HCID 66925065, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Using tert-butyl {[5-bromo-1-(2-cyanophenyl)sulfonyl-1H-pyrrol-3-yl]methyl}methylcarbamate (296 mg), 3-pyridineboronic acid (162 mg), sodium carbonate (208 mg) and tetrakis(triphenylphosphine)palladium (38.2 mg), a procedure as in Reference Example 267 was performed to give the title compound as a white solid (yield 187 mg, 63%).

Sources & evidence

ORD record
ord-d6ebc33456604a81ac90fab6642eaf64
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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