Triethylamine → Tert-butyl 3-(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)prop-2-ynyl(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)carbamate

HRID 1247600Notes

Reaction equation

HRID 1247600 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16](Br)[CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Si:23]([O:30][CH2:31][CH2:32][N:33]([CH2:41][C:42]#[CH:43])[C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].C(N(CC)CC)C>[Cu]I.C(#N)C>[C:1]12([CH2:11][NH:12][C:13]([C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([C:43]#[C:42][CH2:41][N:33]([CH2:32][CH2:31][O:30][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:25])[C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:37])[CH3:38])[CH:15]=3)=[O:22])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11324466tert-Butyl (2-((tert-butyldimethylsilyl)oxy)ethyl)(prop-2-yn-1-yl)carbamateHCID 11773529N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide

Product 1

HCID 69539588Tert-butyl 3-(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)prop-2-ynyl(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)carbamateYield 47.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Procedure

The sub-titled compound was prepared from N-(1 adamantylmethyl)-2-bromo-5-chloroisonicotinamide (Example 2(i)) (0.37 g), tert-butyl (2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)prop-2-yn-1-ylcarbamate (Example 11(i)) (0.54 g), copper (I) iodide (0.004 g), bis-triphenyphosphine palladium dichloride (0.014 g), triethylamine (6 ml) and anhydrous acetonitrile (6 ml) by the method of Example 2(iii). The crude product was purified by chromatography on silica gel eluting with, iso-hexane:ethyl acetate (8:1 to 4:1) to afford the sub-titled compound (0.28 g) as a yellow gum.

Workup

  1. customThe crude product was purified by chromatography on silica gel eluting with, iso-hexane:ethyl acetate (8:1 to 4:1)

Sources & evidence

ORD record
ord-f4dc023fc5f34f59b6e31647b70a9856
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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