Sodium Carbonate → Methyl 5-phenyl-4-propyl-1H-pyrrole-3-carboxylate

HRID 554239Notes

Reaction equation

HRID 554239 reaction equation
Br[C:2]1[N:6](S(C2C=CC=CC=2)(=O)=O)[CH:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[C:3]=1[CH2:20][CH2:21][CH3:22].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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:23]1([C:2]2[NH:6][CH:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[C:3]=2[CH2:20][CH2:21][CH3:22])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 66924749Methyl 5-bromo-1-(phenylsulfonyl)-4-propyl-1H-pyrrole-3-carboxylate

Product 1

HCID 66924692Methyl 5-phenyl-4-propyl-1H-pyrrole-3-carboxylateYield 80.2%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Using methyl 5-bromo-1-(phenylsulfonyl)-4-propyl-1H-pyrrole-3-carboxylate (3.96 g), phenylboronic acid (2.5 g), tetrakis(triphenylphosphine)palladium (1.79 g) and sodium carbonate (3.28 g), a procedure as in Reference Example 56 was performed to give the title compound as a pale-yellow oil (yield 2.0 g, 80%).

Sources & evidence

ORD record
ord-dc0bb1b1aac84e6986ac1fcc6dabc8e9
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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