Sodium hydride → 5-tert-butyl-2-methyl-2H-pyrazole-3-carboxylic acid (2-bromo-5-nitro-pyridin-4-yl)-amide

HRID 570275Notes

Reaction equation

HRID 570275 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[H-].[Na+].[C:14]([C:18]1[CH:19]=[C:20]([C:24](Cl)=[O:25])[N:21]([CH3:23])[N:22]=1)([CH3:17])([CH3:16])[CH3:15]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:24]([C:20]2[N:21]([CH3:23])[N:22]=[C:18]([C:14]([CH3:16])([CH3:15])[CH3:17])[CH:19]=2)=[O:25])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27356843-(Tert-Butyl)-1-Methyl-1H-Pyrazole-5-Carbonyl ChlorideHCID 130404032-Bromo-5-nitropyridin-4-amine

Product 1

HCID 866574325-tert-butyl-2-methyl-2H-pyrazole-3-carboxylic acid (2-bromo-5-nitro-pyridin-4-yl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-bromo-5-nitro-pyridin-4-ylamine (62 mg, 0.28 mmol) in THF (5 mL), was treated with NaH (34 mg, 0.85 mmol) under Ar. The resulting solution was stirred for 10 min and then treated with 5-tert-butyl-2-methyl-2H-pyrazole-3-carbonyl chloride (62 mg, 0.31 mmol) in THF (1 mL). The resulting mixture was stirred at room temperature for 1 h. The resulting mixture was purified by direct application to silica preparative TLC plates (2000 micron) and eluted with 3:7 EtOAc-hexanes to yield 5-tert-butyl-2-methyl-2H-pyrazole-3-carboxylic acid (2-bromo-5-nitro-pyridin-4-yl)-amide. 1H-NMR (400 MHz, CDCl3) δ: 11.2 (s, 1H), 9.18 (s, 1H), 9.11 (s, 1H), 6.65 (s, 1H). 4.18 (s, 1H), 1.34 (s, 9H).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 1 h
  2. customThe resulting mixture was purified by direct application to silica preparative TLC plates (2000 micron)
  3. washeluted with 3:7 EtOAc-hexanes

Sources & evidence

ORD record
ord-ab4f46bd176d447fb578dea012758188
Source dataset
uspto-grants-2015_05
Patent number
US09023846B2

Reaction notes

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