Sodium Carbonate → HCID 67341024, compound

HRID 1669264Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][NH:6][C:7](=[O:24])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][C:17]=2[CH3:23])=[CH:10][CH:9]=1.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][NH:6][C:7](=[O:24])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:18][C:17]=2[CH3:23])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-[4-(4-bromo-2-methyl-benzyloxy)-benzoylamino]-propionic acid methyl ester (0.20 g, 0.49 mmol), phenyl boronic acid (0.09 g, 0.78 mmol), and Na2CO3 (0.11 g, 1.08 mmol) in toluene/water (3 mL: 1 mL) is degassed (2×). Pd(PPh3)4 (0.05 g, 0.04 mmol) is added, and the mixture is stirred at 100° C. for 12 h. The mixture is filtered through Celite. Water is added, and the mixture is extracted with EtOAc. The organics are dried with MgSO4 and concentrated. The crude material is purified by flash chromatography to yield 0.20 g (100%) of the title compound.

Workup

customis degassed (2×)
filtrationThe mixture is filtered through Celite
additionWater is added
extractionthe mixture is extracted with EtOAc
dry with materialThe organics are dried with MgSO4
concentrationconcentrated
customThe crude material is purified by flash chromatography

Sources & evidence

ORD record: ord-0521afb4803247cd8a680f47266b44be
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989457B2

Reaction notes

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