Pyridine → HCID 67994994, compound

HRID 2361350Notes

Reaction equation

HRID 2361350 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH3:11][N:12]([CH3:22])[C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.N1C=CC=CC=1>ClCCCl.C(OCC)(=O)C>[C:5]([C:4]1[C:3]([F:10])=[C:2]([NH:1][C:17](=[O:18])[C:16]2[CH:15]=[CH:14][C:13]([N:12]([CH3:11])[CH3:22])=[CH:21][CH:20]=2)[CH:9]=[CH:8][CH:7]=1)#[N:6]

Participants

6

Reactant 3

HCID 1049PyridineHCID 44007824-(Dimethylamino)benzoyl chlorideHCID 407874923-Amino-2-fluorobenzonitrile

Product 1

HCID 67994994HCID 67994994, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 3-amino-2-fluorobenzonitrile (2.24 g, 16.46 mmol) and 4-(dimethylamino)benzoyl chloride (3.46 g, 18.84 mmol) in 1,2-dichloroethane (50 mL) at rt was added pyridine (0.891 mL, 11.02 mmol). The resulting mixture was heated at 70° C. for 5 hr. On cooling to room temperature, the mixture was diluted with ethyl acetate (250 mL), washed with water (5×60 mL) and brine (60 mL), and dried over anhydrous MgSO4. The organic solution was concentrated under vacuum, and the residue was subjected to ISCO (2×330 g silica gel, 25-50% ethyl acetate/hexane) to afford the desired product (4.11 g, 14.51 mmol, 88% yield) as a white solid.

Workup

  1. temperatureOn cooling to room temperature
  2. washwashed with water (5×60 mL) and brine (60 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationThe organic solution was concentrated under vacuum

Sources & evidence

ORD record
ord-e61336875d434f3cadce119c4d70a1f6
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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