Acetonitrile → HCID 59305375, compound

HRID 2240946Notes

Reaction equation

HRID 2240946 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[CH:15])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[F:17][CH:18]([F:27])[O:19][C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=1.CCN(CC)CC.C(#N)C>CCOC(C)=O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[C:15][C:23]2[CH:24]=[CH:25][C:20]([O:19][CH:18]([F:27])[F:17])=[CH:21][CH:22]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 27370081-(Difluoromethoxy)-4-iodobenzeneHCID 11275982tert-Butyl 3-ethynylphenylcarbamate

Product 1

HCID 59305375HCID 59305375, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (3-ethynyl-phenyl)-carbamic acid tert-butyl ester (14.7 g, 67.7 mmol), 1-difluoromethoxy-4-iodo-benzene (18.2 g, 67.7 mmol), NEt3 (47 mL, 338 mmol), acetonitrile (225 mL), CuI (1.29 g, 6.77 mmol), and Pd(PPh3)2Cl2 (2.85 g, 4.05 mmol) was heated to 60° C. for 1 h. The reaction was diluted with EtOAc/Hex (1:10) and then passed through a pad of silica gel and concentrated and purified with chromatography using hexanes/ethyl acetate (10:1) as the eluting solvents gave the title compound (24.3 g, 100%), characterized by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated
  2. custompurified with chromatography

Sources & evidence

ORD record
ord-12a06630d88a42338b6a01cba6fc25ae
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

Loading…