Potassium Carbonate → 1-(4-Cyclopropylpyridin-3-yl)-3-(2-cyclopropylpyridin-4-yl)imidazolidin-2-one

HRID 572444Notes

Reaction equation

HRID 572444 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:18]=3[CH:19]3[CH2:21][CH2:20]3)[C:9]2=[O:22])[CH:5]=[CH:4][N:3]=1.[CH:23]1(B(O)O)[CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C(C)=CC=CC=1>[CH:19]1([C:18]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:10]2[CH2:11][CH2:12][N:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH:23]4[CH2:25][CH2:24]4)[CH:7]=3)[C:9]2=[O:22])[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 665764121-(2-Chloropyridin-4-yl)-3-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 665768131-(4-Cyclopropylpyridin-3-yl)-3-(2-cyclopropylpyridin-4-yl)imidazolidin-2-oneYield 33.48%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolvent

Procedure

1-(2-chloropyridin-4-yl)-3-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-39a: 220 mg, 0.7 mmol) was reacted with cyclopropyl boronic acid (72 mg, 0.84 mmol), Pd(PPh3)4 (41 mg, 0.035 mmol), potassium carbonate (194 g, 1.4 mmol) and xylene (10 mL) in seal tube at 125° C. for 14 hours. Purification by column chromatography on silica gel (1% methanol in chloroform) afforded 75 mg of the product (33.48% yield).

Workup

  1. customPurification by column chromatography on silica gel (1% methanol in chloroform)

Sources & evidence

ORD record
ord-2096f946b17f4b63a140e1b07a07bc05
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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