Diisopropylethylamine → HCID 10237571, compound

HRID 352656Notes

Reaction equation

HRID 352656 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)[C:5]2=[O:22].C(N(C(C)C)CC)(C)C.[C:32]1([CH2:38][C:39]#[CH:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)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>[O:22]=[C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:40]#[C:39][CH2:38][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:3]=2)[N:8]=[CH:7][N:6]1[CH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1

Participants

8

Reactant 3

HCID 81531DiisopropylethylamineHCID 575753BenzylacetyleneHCID 22482208HCID 22482208, compound

Product 1

HCID 10237571HCID 10237571, compoundYield 77.2%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the compound obtained in Step 1 (0.3 g, 0.739 mmol) in 6.5 ml of DMF, is added diisopropylethylamine (0.381 g, 2.96 mmol), CuI (catalytic amount), 3-phenyl-1-propyne (0.120 g, 1.03 mmol), and Pd(PPh3)2Cl2 (catalytic amount). The reaction mixture is heated to 50° C. for 4 hours. The mixture is then diluted with 150 ml of EtOAc, and washed with 3×100 ml of water, 1×100 ml of brine. The organic layer is then dried over MgSO4, and filtered. The filtrate is concentrated in vacuo. The crude product is triturated with a mixture of hexane/ethyl acetate: 8/1 to yield 225 mg of the pure desired product as a light yellow solid.

Workup

  1. washwashed with 3×100 ml of water, 1×100 ml of brine
  2. dry with materialThe organic layer is then dried over MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. customThe crude product is triturated with a mixture of hexane/ethyl acetate

Sources & evidence

ORD record
ord-64ea57c297844a43aad9af9e265faa12
Source dataset
uspto-grants-2004_06
Patent number
US06747147B2

Reaction notes

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