Pyridine → HCID 66799887, compound

HRID 589675Notes

Reaction equation

HRID 589675 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10](Cl)(=[O:12])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1.[NH2:16][C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21].N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:16][C:17]3[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=3)[C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:12])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11400Ethyl 3-aminobenzoateHCID 27355915-bromo-3-methyl-1-benzothiophene-2-sulfonyl chloride2×

Product 1

HCID 66799887HCID 66799887, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-bromo-3-methyl-benzothiophene-2-sulfonyl chloride (Intermediate 10) (1.00 g, 3.26 mmol), ethyl 3-aminobenzoate (550 mg, 3.33.mmol) and pyridine (3 mL) in CH2Cl2 (150 mL) was stirred at room temperature overnight. The reaction was diluted with CH2Cl2, washed with water and aqueous HCl, dried and concentrated. The residue was purified on silica, using CH2Cl2 as eluent, resulting in 532 mg (36%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.34 (t, J=7.09 Hz, 3 H) 2.44 (s, 3 H) 4.34 (q, J=7.09 Hz, 2 H) 6.85 (s, 1H) 7.36 (dd, J=8.03, 7.62 Hz, 1 H) 7.43 (ddd, J=8.03, 2.26, 1.25 Hz, 1 H) 7.57 (dd, J=8.66, 1.88 Hz, 1 H) 7.65 (dd, J=8.66, 0.50 Hz, 1 H) 7.72 (dd, J=2.26, 1.63 Hz, 1 H) 7.84 (ddd, J=7.62, 1.63, 1.25 Hz, 1 H) 7.87 (dd, J=1.88, 0.50 Hz, 1 H). MS (ESI+) m/z 454 [M+H]+.

Workup

  1. washwashed with water and aqueous HCl
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified on silica

Sources & evidence

ORD record
ord-93db3ebe5c2e44dc82bb6f21141379c0
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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