Potassium Carbonate → HCID 86761328, compound

HRID 2420923Notes

Reaction equation

HRID 2420923 reaction equation
[F:1][C:2]1([F:17])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH2:16])=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.B([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](O)=O)(O)O.[C:30](=[O:33])([O-])[O-:31].[K+].[K+]>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]>[F:17][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][N:16]4[CH:14]=[CH:11][CH:9]=[C:8]([CH3:7])[CH:24]4[C:23]4[C:27]([C:30]([OH:31])=[O:33])=[CH:28][CH:29]=[CH:21][CH:22]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339573-Carboxyphenylboronic acidHCID 86689941HCID 86689941, compound

Product 1

HCID 86761328HCID 86761328, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

N-(6-Chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl cyclopropanecarboxamide (37 mg, 0.10 mmol) was dissolved in 1 mL of DMF in a reaction tube. 3-Boronobenzoic acid (25 mg, 0.15 mmol), 0.2 mL of an aqueous 2 M potassium carbonate solution, and Pd(dppf)Cl2 (8 mg) were added and the reaction mixture was heated for 10 min at 150° C. in the microwave. The reaction mixture was filtered and purified by reverse-phase preparative liquid chromatography to yield 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid. ESI-MS m/z calc. 452.4, found 453.3 (M+1)+. Retention time 1.93 minutes.

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified by reverse-phase preparative liquid chromatography

Sources & evidence

ORD record
ord-22a2da190b2649d09db2844c547c3137
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

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