Pyridine → HCID 3734435, compound

HRID 1405084Notes

Reaction equation

HRID 1405084 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].N1C=CC=CC=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C1COCC1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 678524-Bromo-3-(trifluoromethyl)aniline

Product 1

HCID 3734435HCID 3734435, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-3-(trifluoromethyl)aniline (5.0 g, 20.8 mmol) and pyridine (16.9 mL, 208 mmol) in THF (60 mL) was treated slowly with methanesulfonyl chloride (2.10 mL, 27.1 mmol). The resulting yellow solution was stirred at room temperature for 2 hours, concentrated to dryness and then evaporated twice from toluene to afford syrup. The crude material was purified by silica gel chromatography eluting with 0% to 10% acetone in CH2Cl2 to afford Intermediate 52A (6.6 g, 100% yield) as a white solid. HPLC Ret timed: 3.32 min. MS: m/z=318, 320 [M+H]+; 1H NMR (500 MHz, CD3OD) δ ppm 7.80-7.75 (1 H, d), 7.63 (1 H, brs), 7.43-7.37 (1 H, d), 3.03 (3 H, s).

Workup

  1. concentrationconcentrated to dryness
  2. customevaporated twice from toluene
  3. customto afford syrup
  4. customThe crude material was purified by silica gel chromatography
  5. washeluting with 0% to 10% acetone in CH2Cl2

Sources & evidence

ORD record
ord-1d2b36f3fe154c71ac4bc7e4105231d4
Source dataset
uspto-grants-2014_12
Patent number
US08916553B2

Reaction notes

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