Sodium hydride → HCID 90418776, compound

HRID 1486812Notes

Reaction equation

HRID 1486812 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][C:5]=1[F:11].F[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20]>C1COCC1>[Cl:3][C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][C:18]=2[N+:19]([O-:21])=[O:20])=[CH:6][C:5]=1[F:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27365114-Chloro-3-fluoroanilineHCID 27629103-Fluoro-4-nitropyridine

Product 1

HCID 90418776HCID 90418776, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (422 mg, 60% dispersion in mineral oil, 10.6 mmol) was suspended in THF (20 mL) and 4-chloro-3-fluoroaniline (1.54 g, 10.6 mmol) and 3-fluoro-4-nitropyridine (500 mg, 3.52 mmol) were added. The reaction mixture was stirred for 18 h, quenched with sat aq NH4Cl (2 mL), and concentrated in vacuo. The residue was partitioned between water (50 mL) and DCM (50 mL) and the organic fraction was dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound (207 mg, 22.0%) as an orange solid. LCMS (ES+): 268.0 [MH]+.

Workup

  1. customquenched with sat aq NH4Cl (2 mL)
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between water (50 mL) and DCM (50 mL)
  4. dry with materialthe organic fraction was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-38746f7c60304a2db2ffa6203eb7c930
Source dataset
uspto-grants-2016_08
Patent number
US09428498B2

Reaction notes

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