Sodium Carbonate → HCID 67254651, compound

HRID 536620Notes

Reaction equation

Br[C:2]1[S:6][CH:5]=[C:4]([CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])[C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:15]=1[CH3:22].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:3]2[C:4]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][S:6][C:2]=2[C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)=[C:15]([CH3:22])[CH:16]=1)#[N:21]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl 3-(5-bromo-4-(4-cyano-2-methylphenyl)thiophen-3-yl)propanoate (35 mg, 0.09 mmol), 4-methoxyphenylboronic acid (16 mg, 0.10 mmol), Na2CO3 (19 mg, 0.18 mmol), Pd(PPh3)2Cl2 (6 mg, 0.009 mmol) in a mixture of dioxane and H2O (5 mL, 4:1) was stirred at 100° C. overnight under nitrogen. The mixture was neutralized to pH=5, and extracted with EtOAc. The organic layer was concentrated, and purified by preparative TLC to give 3-(4-(4-cyano-2-methylphenyl)-5-(4-methoxyphenyl)thiophen-3-yl)propanoic acid (30 mg, yield 86%) as yellow oil.

Workup

extractionextracted with EtOAc
concentrationThe organic layer was concentrated
custompurified by preparative TLC

Sources & evidence

ORD record: ord-c57bcea54dae4df4b3ce1b5a048dc67f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859611B2

Reaction notes

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