Diisopropylamine → HCID 58952079, compound

HRID 597877Notes

Reaction equation

HRID 597877 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=1)[CH2:8][C:9]#[CH:10])([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1.N(C(C)C)C(C)C>ClCCl.CCOCC.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.[Cu]I>[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:8][C:9]#[C:10][C:25]1[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 3

HCID 7912DiisopropylamineHCID 125101-Chloro-4-iodobenzeneHCID 58952443HCID 58952443, compound

Product 1

HCID 58952079HCID 58952079, compoundYield 58.2%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (3,4-difluoro-benzyl)-prop-2-ynyl-carbamic acid tert-butyl ester (3.2 g, 11.4 mmol), 4-chloroiodobenzene (4.1 g, 17.2 mmol, 1.5 eq.), Pd(PPh3)2Cl2 (0.4 g. 0.57 mmol, 5 mol %), iPr2NH (4 mL, 28.5 mmol, 2.5 eq.) and CuI (0.435 g, 2.3 mmol, 0.2 eq.) in 100 mL dichloromethane was stirred overnight at room temperature. The solution was diluted with 300 mL ether and filtered through a CELITE pad to remove the insoluble components. The filtrate washed with 2×100 mL 1N HCl, 100 mL brine, dried over MgSO4, filtered, concentrated and chromatographed with 6% ethyl acetate in hexanes to provide 2.6 g of [3-(4-chloro-phenyl)-prop-2-ynyl]-(3,4-difluoro-benzyl)-carbamic acid tert-butyl ester.

Workup

  1. filtrationfiltered through a CELITE pad
  2. customto remove the insoluble components
  3. washThe filtrate washed with 2×100 mL 1N HCl, 100 mL brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed with 6% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ec745e625e0a4125af932b0247054415
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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