5-Hexynenitrile → HCID 178510972, compound

HRID 2289958Notes

Reaction equation

HRID 2289958 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18](I)=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1.[C:25](#[N:31])[CH2:26][CH2:27][CH2:28][C:29]#[CH:30]>C(NCC)C.[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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([C:30]#[C:29][CH2:28][CH2:27][CH2:26][C:25]#[N:31])=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 1398525-HexynenitrileHCID 178522917HCID 178522917, compound

Product 1

HCID 178510972HCID 178510972, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

To a solution of the title compound of Example 5 (0.35 g), CuI (0.042 g), and Pd(PPh3)2Cl2 (0.012 g) in 10 mL diethylamine is added 5-hexynenitrile (0.085 mL). The reaction is stirred overnight. The reaction is then partitioned between ethyl acetate and water. The organic layer is washed twice with water, dried over MgSO4, filtered, and adsorbed onto silica. A Biotage Flash 40S (eluent 3% MeOH:CH2Cl2) affords the desired product. The product is recrystallized from CH2Cl2 --MeOH/hexanes. A second crop of crystals is obtained by concentration of the filtrate. The total yield of the title compound is 0.21 g.

Workup

  1. customThe reaction is then partitioned between ethyl acetate and water
  2. washThe organic layer is washed twice with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-8e626f8a57e64fa7a16c7f6c41c5e46d
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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