Diisopropylethylamine → N-(6-Bromo-1H-indazol-4-yl)-2-pyridinecarboxamide

HRID 1615983Notes

Reaction equation

HRID 1615983 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[CH:6]=[N:7][NH:8][C:9]=2[CH:10]=1.Cl.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](Cl)=[O:20].CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([NH:11][C:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=2)=[O:20])[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 247280636-Bromo-1H-indazol-4-amine

Product 1

HCID 58255852N-(6-Bromo-1H-indazol-4-yl)-2-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-bromo-1H-indazol-4-amine (available from Sinova, 100 mg, 0.47 mmol), 2-pyridinecarbonyl chloride hydrochloride (available from Apollo, 100 mg, 0.71 mmol), DIPEA (0.164 ml) in DCM (10 ml) was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo. Purification by Mass Directed Automated Preparative HPLC (Method B) gave after evaporation of solvents the title compound (38 mg) as a white solid. LCMS (Method B) Rt=0.97 mins, MH+=318.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customPurification by Mass Directed Automated Preparative HPLC (Method B)
  3. customgave
  4. customafter evaporation of solvents the title compound (38 mg) as a white solid

Sources & evidence

ORD record
ord-96ef89c4bf0441d4bee38d25658af74c
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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