Diisopropylethylamine → HCID 10172898, compound

HRID 352657Notes

Reaction equation

HRID 352657 reaction equation
I[C:2]1[N:22]=[CH:21][C:5]2[N:6]=[CH:7][N:8]([CH2:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=3)[C:9](=[O:10])[C:4]=2[CH:3]=1.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>[C:32]1([CH2:38][C:39]#[C:40][C:2]2[N:22]=[CH:21][C:5]3[N:6]=[CH:7][N:8]([CH2:11][C:12]4[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=4)[C:9](=[O:10])[C:4]=3[CH:3]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

8

Reactant 3

HCID 81531DiisopropylethylamineHCID 575753BenzylacetyleneHCID 22482181HCID 22482181, compound

Product 1

HCID 10172898HCID 10172898, compound

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 (0.739 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 warmed 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 8/1: hexane/EtOAc to yield the desired compound.

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 8/1

Sources & evidence

ORD record
ord-eef0577e9fe14f76975a841e37c3ac20
Source dataset
uspto-grants-2004_06
Patent number
US06747147B2

Reaction notes

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