Diisopropylamine → 4-[2-(2-Hydroxyethyl)-1-benzofuran-5-yl]benzonitrile

HRID 2416131Notes

Reaction equation

HRID 2416131 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1I.[CH2:17]([OH:21])[CH2:18][C:19]#[CH:20].P.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(NC(C)C)(C)C>C(OC(C)C)(=O)C.[Pd].[Cu]I>[OH:21][CH2:17][CH2:18][C:19]1[O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=3)=[CH:4][C:3]=2[CH:20]=1

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 11776TriphenylphosphineHCID 135663-Butyn-1-OLHCID 24404PhosphineHCID 103586764-(4-Hydroxy-3-iodophenyl)benzonitrile

Product 1

HCID 114824394-[2-(2-Hydroxyethyl)-1-benzofuran-5-yl]benzonitrile

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 7915Isopropyl AcetateSolvent

Procedure

treating 4′-hydroxy-3′-iodo-1,1′-biphenyl-4-carbonitrile with 3-butyn-1-ol, a palladium source with a phosphine for the palladium and a metal halide in the presence of a base, for example using palladium(ll) acetate, triphenylphosphine, copper(I) iodide in the presence of diisopropylamine, in isopropyl acetate to provide 4-[2-(2-hydroxyethyl)-1-benzofuran-5-yl]benzonitrile;

Sources & evidence

ORD record
ord-a749ea9df7734388ae54dd2af57e057c
Source dataset
uspto-grants-2004_11
Patent number
US06822101B2

Reaction notes

Loading…