Potassium Carbonate → Methyl 5-(2-{[(t-butoxycarbonyl)amino]methyl}-4-methoxyphenyl)-2-methoxybenzoate

HRID 2247433Notes

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]1[CH:30]=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(COC)OC>[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:28]1[CH:29]=[CH:30][C:21]([O:20][CH3:19])=[C:22]([CH:27]=1)[C:23]([O:25][CH3:26])=[O:24])=[O:12])([CH3:11])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 80 °C

Procedure

570 mg of t-butyl N-(2-bromo-5-methoxybenzyl)carbamate, 440 mg of methyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, 86 mg of dichlorobistriphenyl phosphinoferrocene palladium and 1.0 g of potassium carbonate were dissolved in 15 ml of dimethoxyethane, and the mixture was heated at 80° C. for 24 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 680 mg of the title compound in the 3:1 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-8f219ca6433f421cab9d4cb26e076161
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687664B2

Reaction notes

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