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

HRID 1472286Notes

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-6c39c2dbc83749258302ecc272e595fb
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012485B2

Reaction notes

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