Sodium hydride → 4-(6-bromo-1H-indazol-1-yl)-N-(2-methoxypyridin-3-yl)-1,3,5-triazin-2-amine

HRID 1398499Notes

Reaction equation

HRID 1398499 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:14]1[N:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]2[C:22]([O:27][CH3:28])=[N:23][CH:24]=[CH:25][CH:26]=2)[N:15]=1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[C:14]2[N:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]3[C:22]([O:27][CH3:28])=[N:23][CH:24]=[CH:25][CH:26]=3)[N:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 178424716-Bromo-1H-indazoleHCID 866695704-chloro-N-(2-methoxypyridin-3-yl)-1,3,5-triazin-2-amine

Product 1

HCID 681817474-(6-bromo-1H-indazol-1-yl)-N-(2-methoxypyridin-3-yl)-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-1H-indazole (172 mg, 0.87 mmol) in DMF (8 mL) was added NaH (60% in oil, 69.8 mg, 1.75 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 10 minutes before the addition of 4-chloro-N-(2-methoxypyridin-3-yl)-1,3,5-triazin-2-amine (311.18 mg, 1.31 mmol). Stirring was continued at RT for 2 hr. The reaction mixture was quenched with water and EtOAc added. The resultant precipitate was collected and further drying under vacuum gave the title compound as a beige solid; 1H NMR (250 MHz, CDCl3) δ 4.09 (3H, s), 7.05 (1H, d, J=2.28 Hz), 7.50 (1H, dd, J=8.53, 1.68 Hz), 7.62-7.70 (1H, m), 7.88-8.09 (2H, m), 8.30 (1H, d, J=0.76 Hz), 8.74 (1H, dd, J=7.77, 1.68 Hz), 8.83 (1H, s), 9.01 (1H, s); LC-MS: m/z=+397.9/399.8 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with water and EtOAc
  2. additionadded
  3. customThe resultant precipitate was collected
  4. customfurther drying under vacuum

Sources & evidence

ORD record
ord-539216283c7e435fa971a545ce4567a3
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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