Sodium Carbonate → HCID 66924994, compound

HRID 554354Notes

Reaction equation

HRID 554354 reaction equation
Br[C:2]1[N:6]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:5]=[C:4]([CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:3]=1[CH:26]([CH3:28])[CH3:27].[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=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>[CH:26]([C:3]1[C:4]([CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[CH:5][N:6]([S:7]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)(=[O:8])=[O:9])[C:2]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 66924874HCID 66924874, compound

Product 1

HCID 66924994HCID 66924994, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Using tert-butyl {[5-bromo-4-isopropyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (596 mg), phenylboronic acid (307 mg), tetrakis(triphenylphosphine)palladium (218 mg) and sodium carbonate (401 mg), a procedure as in Reference Example 56 was performed to give the title compound as a pale-red oil (yield 218 mg, 37%).

Sources & evidence

ORD record
ord-1b4dc58d898b41acb36fef64233f8b99
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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