Pyridine → HCID 86730428, compound

HRID 871176Notes

Reaction equation

HRID 871176 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([NH2:10])=[CH:7][CH:8]=[CH:9][C:2]1=2.N1C=CC=CC=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([NH:10][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 2984844-Aminobenzo[b]thiophene

Product 1

HCID 86730428HCID 86730428, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of benzo[b]thiophen-4-amine (1 g, 6.70 mmol) and pyridine (1.355 mL, 16.75 mmol) in CH2Cl2 (15 mL) was added dropwise methanesulfonyl chloride (0.574 mL, 7.37 mmol) at 0° C. under nitrogen atmosphere. The reaction mixture was then allowed to warm to room temperature while stirring overnight. The reaction mixture was washed with saturated sodium bicarbonate solution, water, brine and dried over sodium sulfate. Evaporation of the solvent furnished a crude residue, which was subjected to BIOTAGE® (100% methylene chloride) to give the title compound as a white solid (1.2 g, 79%). LC/MS: Example 105A @ 2.88 min (RT) (Condition H). MS (ES): m/z=226.0, [M+H]+. 1H NMR (400 MHz, MeOD) δ ppm 7.77 (1 hr, d, J=7.81 Hz), 7.59 (2 hr, d, J=1.26 Hz), 7.25-7.42 (2 hr, m), 2.94 (3 hr, s).

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution, water, brine
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of the solvent
  4. customfurnished a crude residue, which

Sources & evidence

ORD record
ord-9217aac7133b4849b482f9cd6a897988
Source dataset
uspto-grants-2015_03
Patent number
US08969586B2

Reaction notes

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