Diisopropylethylamine → HCID 86648964, compound

HRID 449929

Reaction equation

HRID 449929 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Br:8])[CH:3]=1.C(N(C(C)C)CC)(C)C.[Cl:18][C:19]1[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[C:24]([F:30])[C:20]=1[C:21](Cl)=[O:22]>ClCCl.CC#N>[Br:8][C:4]1[CH:3]=[C:2]([NH:1][C:21](=[O:22])[C:20]2[C:24]([F:30])=[CH:25][C:26]([C:28]#[N:29])=[CH:27][C:19]=2[Cl:18])[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 3464554-Amino-2-bromopyridineHCID 866489652-Chloro-4-cyano-6-fluorobenzoyl chloride

Product 1

HCID 86648964HCID 86648964, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) solution of 4-amino-2-bromopyridine (346 mg, 2.0 mmol) and diisopropylethylamine (461 mg, 4.0 mmol) in dichloromethane (5 mL) and CH3CN (0.5 mL) was added a solution of 2-chloro-4-cyano-6-fluorobenzoyl chloride (484 mg, 2.2 mmol) in dichlormethane (5 mL) drop wise. The reaction mixture was warmed up to room temperature and stirred for 16 hours. The reaction was quenched with saturated NH4Cl (40 mL) and extracted with EtOAc (3×50 mL). The combined organic extractss were dried with Na2SO4 and concentrated under reduced pressure. The residue wars purified by silica gel column chromatography (0-50% EtOAc/hexane) to give N-(2-bromopyridin-4-yl)-2-chloro-4-cyano-6-fluorobenzamide as an off-white solid (379 mg, yield: 53%).

Workup

  1. customThe reaction was quenched with saturated NH4Cl (40 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe combined organic extractss were dried with Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue wars purified by silica gel column chromatography (0-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-c2f844975da0402cbe3c51f97dd0fb00
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Linked notes

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