Sodium Carbonate → HCID 57483849, compound

HRID 384401Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8](Br)[O:7][C:6]=1[CH3:11])=[O:4].[CH3:12][O:13][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[CH:16][C:15]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([N+:20]([O-:22])=[O:21])[C:14]=2[O:13][CH3:12])[O:7][C:6]=1[CH3:11])=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

5-Bromo-2-methyl-furan-3-carboxylic acid methyl ester 53a (0.65 g, 3.0 mmol) and 2-(2-methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 6a (1.0 g, 3.58 mmol) were dissolved in 1,4-dioxane (15 mL) followed by addition of tetrakis(triphenylphosphine)palladium (173 mg, 0.15 mmol) and sodium carbonate (636 mg, 6.0 mmol). The reaction mixture was heated to reflux at 100° C. for 3 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was cooled and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound 5-(2-methoxy-3-nitro-phenyl)-2-methyl-furan-3-carboxylic acid methyl ester 53b (659 mg, yield 75%) as a white solid.

Workup

temperatureThe reaction mixture was heated
temperatureThe mixture was cooled
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-52eb74cdd4f645b9ac759b90d17fc7ed
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367710B2

Reaction notes

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