Sodium Carbonate → N-{6-[4-(Acetylamino)phenyl]-1H-indazol-4-yl}-2-pyridinecarboxamide

HRID 1695764

Reaction equation

HRID 1695764 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.[C:20]([NH:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(=[O:22])[CH3:21].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]>[C:20]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([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:26][CH:25]=1)(=[O:22])[CH3:21]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27346574-Acetamidophenylboronic acidHCID 58255852HCID 58255852, compound

Product 1

HCID 44540128N-{6-[4-(Acetylamino)phenyl]-1H-indazol-4-yl}-2-pyridinecarboxamide

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 (70 mg, 0.22 mmol), [4-(acetylamino)phenyl]boronic acid (47 mg, 0.26 mmol), Pd(dppf)Cl2 (22 mg, 0.027 mmol) and 2 M sodium carbonate (aq) (0.328 ml, 0.656 mmol) in 1,4-dioxane (1.5 ml) and water (1.5 ml) were heated in a Biotage microwave at 150° C. for 30 mins. The reaction was washed through a silica cartridge eluting with MeOH. The solvent was removed in vacuo. The residue was purified by HPLC using the method described below to afford the title compound.

Workup

  1. washThe reaction was washed through a silica cartridge
  2. washeluting with MeOH
  3. customThe solvent was removed in vacuo
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-68f4808c169241f297964125d7d8c8ee
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Linked notes

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