Water → HCID 61694722, compound

HRID 1623503Notes

Reaction equation

HRID 1623503 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1.O>ClCCl>[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:27][S:8]([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)(=[O:10])=[O:9])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 673264-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 203244745-Bromopyridine-3-sulfonyl chloride

Product 1

HCID 61694722HCID 61694722, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-bromo-3-pyridinesulfonyl chloride (CAS#65001-21-0, 256 mg, 1.0 mmol) in dichloromethane (8 mL) at 0° C. was added diisopropylethylamine (0.350 mL, 2.0 mmol) followed by 4-fluorobenzylamine (CAS#140-75-0, 0.11 mL, 0.95 mmol). The reaction was put at room temperature and stirred for 15 minutes. The reaction was then poured into water and diluted with dichloromethane. The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to furnish 5-bromo-pyridine-3-sulfonic acid 4-fluoro-benzylamide without the need for further purification. MS: (ES+) m/z 344.8 (M+H)+

Workup

  1. customwas put at room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted two additional times with dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7cf8611075034f23a18af54d985d6ca7
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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