Cyclopropylboronic acid → 3-Chloro-2-cyclopropylisonicotinic acid ethyl ester

Reaction equation

[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=1[Cl:12])[CH3:2].[CH:14]1(B(O)O)C[CH2:15]1>>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH:11]2[CH2:15][CH2:14]2)[C:6]=1[Cl:12])[CH3:2]

Participants

Reactant 2

HCID 2760897Cyclopropylboronic acid

HCID 86721905Ethyl 3-chloro-2-methylisonicotinate

Product 1

HCID 712391703-Chloro-2-cyclopropylisonicotinic acid ethyl ester

Procedure

This compound was prepared using a method analogous to that of 3-chloro-2-methylisonicotinic acid ethyl ester (A.2.5.2), cyclopropylboronic acid replacing trimethylboroxine. Purification by CC (KP-SIL™ from Biotage) using Hept/EtOAc (9/1) gives the desired product as colorless oil;

Workup

customThis compound was prepared
customPurification by CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record: ord-5b296ee74e074b4b994864afebd20195
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221832B2

Reaction notes

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