Sodium Carbonate → Ethyl 5-(3,5-di-tert-butylphenyl)-2-methyl-1-(piperidin-1-ylsulfonyl)-1H-pyrrole-3-carboxylate

HRID 1844714Notes

Reaction equation

Br[C:2]1[N:6]([S:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)(=[O:9])=[O:8])[C:5]([CH3:16])=[C:4]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:3]=1.[C:22]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:31]=1)([CH3:25])([CH3:24])[CH3:23].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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:22]([C:26]1[CH:27]=[C:28]([C:2]2[N:6]([S:7]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)(=[O:9])=[O:8])[C:5]([CH3:16])=[C:4]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:3]=2)[CH:29]=[C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:31]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of compound 4b (2.1 g, 5.0 mmol), (3,5-di-tert-butylphenyl)boronic acid (1.9 g, 8.1 mmol), Na2CO3 (1.9 g, 17.9 mmol) and Pd(PPh3)4 (100 mg) in dioxane (50 mL) and H2O (15 mL) was heated to 100° C. for 1 h, evaporated and dissolved in EA. The mixture was washed with water (4×80 mL) and brine, dried with Na2SO4, concentrated and purified by CC to afford compound 4c (1.5 g, 61%) as a right red oil.

Workup

customevaporated
dissolutiondissolved in EA
washThe mixture was washed with water (4×80 mL) and brine
dry with materialdried with Na2SO4
concentrationconcentrated
custompurified by CC

Sources & evidence

ORD record: ord-fa386ef37958475cb1a411af5c0843cd
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946446B2

Reaction notes

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