Thionyl Chloride → HCID 18466631, compound

HRID 2229347Notes

Reaction equation

HRID 2229347 reaction equation
[NH2:1][C:2]1[C:3]([NH:12][CH2:13][CH3:14])=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.C([O-])(O)=O.[Na+].[Br:20][C:21]1[CH:22]=[C:23]([C:28](Cl)=[O:29])[C:24]([Cl:27])=[N:25][CH:26]=1.BrC1C=C(C(O)=O)C(O)=NC=1.O=S(Cl)Cl>CC#N>[Cl:27][C:24]1[C:23]([C:28]([NH:1][C:2]2[C:3]([NH:12][CH2:13][CH3:14])=[N:4][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:6][CH:7]=2)=[O:29])=[CH:22][C:21]([Br:20])=[CH:26][N:25]=1

Participants

7

Reactant 5

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 126772955-Bromo-2-chloro-3-pyridinecarbonyl chlorideHCID 18466603HCID 18466603, compoundHCID 178418525HCID 178418525, compound

Product 1

HCID 18466631HCID 18466631, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a cooled solution of 3-amino-2-(ethylamino)-6-trifluoromethyl pyridine (1 g, 4.9 mmol) in MeCN (24 mL) was added solid NaHCO3 (906 mg, 11 mmol). After 5 min, crude 5-bromo-2-chloro-3-pyridinecarbonyl chloride (prepared from 5-bromo-2-hydroxy-3-pyridinecarboxylic acid and SOCl2 [as described by T. W. Gero et al. in Synth. Commun. 1989,19,553-559 (incorporated herein by reference) but with omission of the aqueous work-up] was added (1 equiv., 4.9 mmol). After 2 h, the reaction mixture was poured over ice/H2O (1.5 L) and the resulting solid was filtered, rinsed with H2O and then hexane. After drying under reduced pressure overnight, the title compound was obtained as a light brown solid (1.6 g, 77% yield).

Workup

  1. additionwas added (1 equiv., 4.9 mmol)
  2. waitAfter 2 h
  3. filtrationthe resulting solid was filtered
  4. washrinsed with H2O
  5. customAfter drying under reduced pressure overnight

Sources & evidence

ORD record
ord-d48d0a3004ad469abe3c19719ada1daf
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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