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

HRID 341406Notes

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-432d7c1b25564fd6a89464a25ad455b1
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895755B2

Reaction notes

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