N,N-Dimethylpropargylamine → HCID 59447599, compound

HRID 1518338Notes

Reaction equation

HRID 1518338 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][N:3]=1.[CH3:17][N:18]([CH3:22])[CH2:19][C:20]#[CH:21]>CN(C=O)C.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>[CH3:17][N:18]([CH3:22])[CH2:19][C:20]#[C:21][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 81643N,N-DimethylpropargylamineHCID 59447608HCID 59447608, compound

Product 1

HCID 59447599HCID 59447599, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of compound 57A (154 mg, 0.593 mmol), N,N-dimethylprop-2-yn-1-amine (0.190 ml, 1.778 mmol), (PPh3)2PdCl2 (62.4 mg, 0.089 mmol), TEA (0.413 ml, 2.96 mmol) in DMF (3 ml) was added copper(I) iodide (11.29 mg, 0.059 mmol). The resulting mixture was heated at 150° C. in a Smith microwave synthesizer for 30 min and purified by flash chromatography to provide the desired compound 57B; LCMS (APCI) m/e 307.

Workup

  1. custompurified by flash chromatography

Sources & evidence

ORD record
ord-aef2c42fbf064ce5be0c3d1e51859775
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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