Sodium Carbonate → 5-(2-aminopyrimidin-4-yl)-2-(2-chloro-5-cyanophenyl)-1H-pyrrole-3-carboxamide

HRID 924682Notes

Reaction equation

HRID 924682 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11](Br)=[C:10]([C:14]([NH2:16])=[O:15])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][C:19]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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]>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[NH:12][C:11]([C:19]3[CH:20]=[C:21]([C:24]#[N:25])[CH:22]=[CH:23][C:18]=3[Cl:17])=[C:10]([C:14]([NH2:16])=[O:15])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27632792-Chloro-5-cyanophenylboronic acidHCID 497882145-(2-aminopyrimidin-4-yl)-2-bromo-1H-pyrrole-3-carboxamide

Product 1

HCID 665710105-(2-aminopyrimidin-4-yl)-2-(2-chloro-5-cyanophenyl)-1H-pyrrole-3-carboxamideYield 13%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

5-(2-Aminopyrimidin-4-yl)-2-bromo-1H-pyrrole-3-carboxamide (prepared according to WO2007/110344, 0.1 g, 0.35 mmol), 2-chloro-5-cyanophenylboronic acid (127 mg, 0.7 mmol), Na2CO3 (111 mg, 1.05 mmol), and PdCl2(dppf) (28 mg, 0.035 mmol) in DME (2.5 mL) and water (1 mL) were heated at 80° C. for 12 h, under argon. After cooling to room temperature, the precipitate was filtered and the filtrate was evaporated under reduced pressure. The crude material was purified by preparative HPLC (Method 1) to afford the title compound (15 mg, 13%).

Workup

  1. filtrationthe precipitate was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe crude material was purified by preparative HPLC (Method 1)

Sources & evidence

ORD record
ord-008ae75dd38741b5b8cd37fd04c35427
Source dataset
uspto-grants-2016_03
Patent number
US09283224B2

Reaction notes

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