Dichloromethane → 1-(5-(3-Chloro-4-cyanophenyl)pyridin-3-yl)cyclopropanecarboxylic acid

HRID 391327Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]2([C:11]([O-:13])=[O:12])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.[K+].[Cl:15][C:16]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[CH:20][C:17]=1[C:18]#[N:19].C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:15][C:16]1[CH:23]=[C:22]([C:2]2[CH:3]=[C:4]([C:8]3([C:11]([OH:13])=[O:12])[CH2:10][CH2:9]3)[CH:5]=[N:6][CH:7]=2)[CH:21]=[CH:20][C:17]=1[C:18]#[N:19]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of potassium 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate (28 mg, 0.1 mmol), 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (26 mg, 0.1 mmol), PdCl2(dppf).CH2Cl2 (4.08 mg, 5.0 μmol) in DMF (1 mL) was added 2M Na2CO3 (0.1 mL, 0.2 mmol), and the mixture was heated to 100° C. for 2 h. The mixture was concentrated and purified by silica chromatography eluting with a 0-10% MeOH-DCM gradient to give 1-(5-(3-chloro-4-cyanophenyl)pyridin-3-yl)cyclopropanecarboxylic acid. MS: (ESI) m/z 299.0, 301.0 (M+H)+.

Workup

concentrationThe mixture was concentrated
custompurified by silica chromatography
washeluting with a 0-10% MeOH-DCM gradient

Sources & evidence

ORD record: ord-0450ff0bb89b4c98a0a5be9f35fd3618
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383827B2

Reaction notes

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