Sodium hydride → HCID 86723311, compound

HRID 2366225Notes

Reaction equation

HRID 2366225 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[Cl:12][C:13]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[C:18]([F:24])[C:14]=1[C:15](Cl)=[O:16]>CN(C=O)C>[Cl:12][C:13]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[C:18]([F:24])[C:14]=1[C:15]([N:9]([C:15](=[O:16])[C:14]1[C:18]([F:24])=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:13]=1[Cl:12])[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=1[F:8])=[O:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 601502892-Chloro-3-fluoropyridin-4-amineHCID 866489652-Chloro-4-cyano-6-fluorobenzoyl chloride

Product 1

HCID 86723311HCID 86723311, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-chloro-3-fluoropyridin-4-ylamine (1.05 g, 7.1 mmol) in DMF (25 mL) at 0° C. was added sodium hydride (0.343 g, 14.3 mmol). The resulting violet mixture stirred for 20 minutes before a solution of 2-chloro-4-cyano-6-fluoro-benzoyl chloride (1.87 g, 8.6 mmol) in DMF (10 mL) was added. The mixture was warmed to room temperature stirred for 16 hours, then quenched with water and 1M HCl. The mixture was filtered through Celite®, washing with EtOAc. The organic filtrate was dried over Na2SO4 and concentrated under reduced pressure. The resultant residue was purified by silica gel flash chromatography eluting with DCM to give the desired compound as an off-white foam (0.869 g, 25% yield). 1H NMR (300 MHz, CDCl3): δ 8.24 (d, J=5.1 Hz, 1H), 7.55 (s, 2H), 7.36 (d, J=8.0 Hz, 2H), 7.32-7.23 (m, 1H).

Workup

  1. additionwas added
  2. customquenched with water and 1M HCl
  3. filtrationThe mixture was filtered through Celite®
  4. washwashing with EtOAc
  5. dry with materialThe organic filtrate was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant residue was purified by silica gel flash chromatography
  8. washeluting with DCM

Sources & evidence

ORD record
ord-fe8da4329c3744f4a8ed96107016a7ce
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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