2-Chlorobenzoic Acid → 4-(Pyridin-2-yl)but-3-ynyl 2-chlorobenzoate

HRID 422506Notes

Reaction equation

HRID 422506 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]#[C:18][CH2:19][CH2:20]O.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:20][CH2:19][C:18]#[C:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=1)=[O:5]

Participants

6

Reactant 3

HCID 83742-Chlorobenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 110080634-(Pyridin-2-yl)but-3-yn-1-ol

Product 1

HCID 665985244-(Pyridin-2-yl)but-3-ynyl 2-chlorobenzoateYield 43.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To solution of 2-chlorobenzoic acid (330 mg, 2.10 mmol), 4-(pyridin-2-yl)but-3-yn-1-ol (310 mg, 2.1 mmol), in DCM (7 mL), was successively added EDCI.HCl (600 mg, 3.2 mmol) and DMAP (13 mg, 0.105 mmol). The resulting mixture was then stirred overnight at ambient temperature. The reaction mixture was concentrated. Purification over silicagel chromatography (prepacked 25 g silicagel column, Cyclohexane/AcOEt: 80/20 as eluent) to afford 260 mg of 4-(pyridin-2-yl)but-3-ynyl 2-chlorobenzoate (Yield: 43%) as a yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customPurification over silicagel chromatography (prepacked 25 g silicagel column, Cyclohexane/AcOEt: 80/20 as eluent)

Sources & evidence

ORD record
ord-62c008715859439694834aa96a4dac63
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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