Sodium Carbonate → HCID 44540218, compound

HRID 1695765Notes

Reaction equation

HRID 1695765 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:13])[CH:3]=1.[CH3:20][NH:21][C:22]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)=[O:23].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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]>[CH3:20][NH:21][C:22]([C:24]1[CH:29]=[C:28]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[N:7][NH:8]3)=[C:4]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[O:13])[CH:3]=2)[CH:27]=[CH:26][CH:25]=1)=[O:23]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27735243-(Methylcarbamoyl)benzeneboronic acidHCID 58255852N-(6-Bromo-1H-indazol-4-yl)-2-pyridinecarboxamide

Product 1

HCID 44540218HCID 44540218, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(6-Bromo-1H-indazol-4-yl)-2-pyridinecarboxamide (100 mg, 0.31 mmol), {3-[(methylamino)carbonyl]phenyl}boronic acid (66 mg, 0.37 mmol), Pd(dppf)Cl2 (31 mg, 0.038 mmol) and 2 M sodium carbonate (aq) (0.468 ml, 0.936 mmol) in 1,4-dioxane (1.5 ml) and water (1 ml) were heated in a Biotage microwave at 150° C. for 30 mins. The reaction was purified by HPLC as follows to give title compound, 7 mg.

Workup

  1. customThe reaction was purified by HPLC

Sources & evidence

ORD record
ord-2a7faf98ed18413f869a98bee90ede37
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

Loading…