Sodium Carbonate → HCID 66576895, compound

HRID 572453Notes

Reaction equation

HRID 572453 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[C:19](Cl)[N:18]=[C:17]([Cl:22])[CH:16]=3)[C:11]2=[O:23])[CH2:3][CH2:2]1.[CH:24]1(B(O)O)[CH2:26][CH2:25]1.C(=O)([O-])[O-].[Na+].[Na+]>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=CC=CC=1>[Cl:22][C:17]1[CH:16]=[C:15]([N:12]2[CH2:13][CH2:14][N:10]([C:5]3[CH:6]=[N:7][CH:8]=[CH:9][C:4]=3[CH:1]3[CH2:3][CH2:2]3)[C:11]2=[O:23])[CH:20]=[C:19]([CH:24]2[CH2:26][CH2:25]2)[N:18]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 66576894HCID 66576894, compound

Product 1

HCID 66576895HCID 66576895, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(4-cyclopropyl pyridin-3-yl)-3-(2,6-dichloropyridin-4-yl)imidazolidin-2-one (I-46a: 100 mg, 0.2865 mmol) was reacted with cyclopropyl boronic acid (74 mg, 0.8593 mmol), Pd(PPh3)4 (7 mg, 0.0057 mmol), sodium carbonate (69 g, 0.6590 mmol) and toluene (5 mL) in seal tube at 120° C. for 12 hours. Purification by column chromatography on silica gel (1% methanol in chloroform), followed by preparative HPLC afforded 20 mg of the product (20% yield).

Workup

  1. customreagents and reaction conditions
  2. customPurification by column chromatography on silica gel (1% methanol in chloroform)

Sources & evidence

ORD record
ord-5d59e9e7eac74e138fd1a8f9f926cc1c
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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