Diisopropylethylamine → Ethyl 3-{[6-(acetylamino)pyridin-3-yl]ethynyl}-4-methylbenzoate

HRID 1255956Notes

Reaction equation

HRID 1255956 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:14]([C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[N:20][CH:21]=1)#[CH:15].C(N(CC)C(C)C)(C)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:23]([NH:22][C:19]1[N:20]=[CH:21][C:16]([C:14]#[C:15][C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=2[CH3:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:17][CH:18]=1)(=[O:25])[CH3:24]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 18007713N-(5-Ethynylpyridin-2-YL)acetamideHCID 23073518Ethyl 3-iodo-4-methylbenzoate

Product 1

HCID 68898058Ethyl 3-{[6-(acetylamino)pyridin-3-yl]ethynyl}-4-methylbenzoate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 3-iodo-4-methylbenzoate (845 mg, 2.9 mmol, 0.8 eq), N-(5-ethynylpyridin-2-yl)acetamide (3.5 mmol, 1.0 eq). Pd(PPh3)4 (51 mg, 0.044 mmol), CuI (20.4 mg, 0.11 mmol), and N,N-diisopropylethylamine (0.8 ml, 4.4 mmol) in 2 ml of DMF is heated at 55° C. (oil bath) for 1 hr under nitrogen. After cooling to r.t., the solvent is evaporated and DCM is added to dissolve the residue. The solution is washed with water and brine, dried and evaporated and the crude material is chromatographed with CombiFlash (DCM/MeOH).

Workup

  1. customthe solvent is evaporated
  2. additionDCM is added
  3. dissolutionto dissolve the residue
  4. washThe solution is washed with water and brine
  5. customdried
  6. customevaporated
  7. customthe crude material is chromatographed with CombiFlash (DCM/MeOH)

Sources & evidence

ORD record
ord-7b6621750c1248e995d0c4d5ac588e8e
Source dataset
uspto-grants-2013_06
Patent number
US08461167B2

Reaction notes

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