Sodium Carbonate → HCID 67507790, compound

HRID 1431713Notes

Reaction equation

HRID 1431713 reaction equation
[NH2:1][C:2]1[C:9]([I:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:3]=1.[H-].[Na+].Cl[C:20]1[C:29]2[C:24](=[CH:25][C:26]([F:31])=[CH:27][C:28]=2[F:30])[N:23]=[C:22]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[C:21]=1[CH3:38].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[F:30][C:28]1[CH:27]=[C:26]([F:31])[CH:25]=[C:24]2[C:29]=1[C:20]([NH:1][C:2]1[C:9]([I:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH:3]=1)=[C:21]([CH3:38])[C:22]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)=[N:23]2

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 596310254-Chloro-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolineHCID 67508051HCID 67508051, compound

Product 1

HCID 67507790HCID 67507790, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A dry flask containing 4-amino-5-iodo-2-morpholinobenzonitrile (140 mg, 0.42 mmol) in dry DMF (3.0 mL) was cooled to 0° C., then sodium hydride, 60% dispersion in mineral oil (34.7 mg, 0.87 mmol) was added carefully in portions. The mixture was stirred at 0° C. for 15 minutes, then 4-chloro-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinoline (185 mg, 0.64 mmol) was added in portions. Upon complete addition, the mixture was warmed to 60° C. After 2.5 h, the reaction was cooled to rt then was carefully treated with 10% sodium carbonate solution. The black mixture was subsequently extracted five times with DCM:methanol (90:10). The organic extraction was then washed one time with brine and dried over anhydrous magnesium sulfate. After filtration and concentration, the black residue was treated with methanol and placed on the rotovap. (without vac.) in a 45° C. water bath. After 30 minutes, the solid was filtered and rinsed twice with methanol to afford an off white solid as 4-(5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-ylamino)-5-iodo-2-morpholinobenzonitrile. Mass Spectrum (pos.) m/e: 583.9 (M+H)+.

Workup

  1. additionUpon complete addition
  2. temperaturethe mixture was warmed to 60° C
  3. waitAfter 2.5 h
  4. temperaturethe reaction was cooled to rt
  5. extractionThe black mixture was subsequently extracted five times with DCM:methanol (90:10)
  6. extractionThe organic extraction
  7. washwas then washed one time with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtration and concentration
  10. additionthe black residue was treated with methanol
  11. customin a 45° C.
  12. waitAfter 30 minutes
  13. filtrationthe solid was filtered
  14. washrinsed twice with methanol

Sources & evidence

ORD record
ord-4c6c0415a18d4177be2644a1e6ea8c64
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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