Potassium Carbonate → Methyl 3-(2-{[(t-butoxycarbonyl)amino]methyl}-4-methoxyphenyl)benzoate

HRID 2247432Notes

Reaction equation

Br[C:2]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:3]=1[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[CH3:19][O:20][C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[C:8]([O:7][C:6]([NH:5][CH2:4][C:3]1[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:2]=1[C:27]1[CH:28]=[C:23]([CH:24]=[CH:25][CH:26]=1)[C:21]([O:20][CH3:19])=[O:22])=[O:12])([CH3:11])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 100 °C

Procedure

1.26 g of t-Butyl N-(2-bromo-5-methoxybenzyl)carbamate, 790 mg of 3-methoxycarbonylphenylboronic acid, 231 mg of tetrakistriphenyl phosphine palladium and 2.20 g of potassium carbonate were dissolved in 25 ml of toluene, and the mixture was heated at 100° C. for 7 hours in a nitrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was evaporated. The residue was purified by silica gel column, to give 470 mg of the title compound in the 4:1 hexane-ethyl acetate fraction.

Workup

filtrationThe reaction mixture was filtered through Celite
customthe filtrate was evaporated
customThe residue was purified by silica gel column

Sources & evidence

ORD record: ord-3d6a6691f918489a885ec7430cfdce98
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687664B2

Reaction notes

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