tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate → HCID 57549750, compound

HRID 1802944Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1[C:10](=[O:19])[NH:11][C:12]([CH2:15][CH2:16][CH2:17][CH3:18])=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[C:26]([O:30][C:31]([C:33]1[C:34]([C:39]2[CH:44]=[CH:43][C:42]([CH2:45]Br)=[CH:41][CH:40]=2)=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>C1COCC1>[C:26]([O:30][C:31]([C:33]1[C:34]([C:39]2[CH:44]=[CH:43][C:42]([CH2:45][N:11]3[C:12]([CH2:15][CH2:16][CH2:17][CH3:18])=[CH:13][CH:14]=[C:9]([CH2:8][NH:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:20])[C:10]3=[O:19])=[CH:41][CH:40]=2)=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: -5 °C

Procedure

(6-Butyl-2-oxo-1,2-dihydropyridin-3-ylmethyl)carbamic acid t-butyl ester (200 mg, 0.71 mmol) was dissolved in THF (5 mL) and cooled to −5° C. n-Butyllithium (285 μL, 2.5M solution in hexanes, 1 eq) was added, and the mixture was stirred at −5° C. for 5 minutes. 4′-Bromomethylbiphenyl-2-carboxylic acid t-butyl ester (247 mg, 1 eq) was added, and solution was warmed to reflux and stirred for 72 hours. The solution was allowed to cool, the solvent evaporated and the residue purified by silica gel chromatography (3:1 hexanes:EtOAc) to yield intermediate (25a) as a white solid (180 mg, 330 μmol). MS m/z: [M+H+] calcd for C33H43N2O5, 547.7. found 547.3.

Workup

additionwas added
temperaturesolution was warmed
temperatureto reflux
stirringstirred for 72 hours
temperatureto cool
customthe solvent evaporated
customthe residue purified by silica gel chromatography (3:1 hexanes:EtOAc)

Sources & evidence

ORD record: ord-2a145c96b3be4ae0a1ea398e4a7b26da
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349875B2

Reaction notes

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