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

HRID 1189323Notes

Reaction equation

HRID 1189323 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-chlorobenzoate

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.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-ee59d823e9f244bb879478475c38a191
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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