Benzenesulfonyl chloride → HCID 68866441, compound

HRID 1725906Notes

Reaction equation

HRID 1725906 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:12])=[CH:4][CH:3]=1.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1.C(Cl)Cl>[Br:11][C:10]1[C:2]([NH:1][S:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:21])=[O:20])=[CH:3][CH:4]=[C:5]2[C:9]=1[C:8](=[O:12])[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 534220646-Amino-7-bromo-2,3-dihydro-1H-inden-1-one

Product 1

HCID 68866441HCID 68866441, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 129C (1.0808 g, 3.52 mmol) in pyridine (17.5 mL) was treated with phenylsulfonyl chloride (0.58 mL, 4.58 mmol), stirred for 2 hours, diluted with CH2Cl2, washed with 1N HCl (3×50 mL) and brine (50 mL), dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel with 9:1 hexanes/ethyl acetate to provide the desired product (450 mg, 35%); MS (ESI(+)) m/e 368 (M+H)+; MS (ESI(−)) m/e 364, 366 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.70 (m, 2H), 7.63 (m, 1H), 7.56 (m, 2H), 7.51 (m, 1H), 7.42 (m, 1H), 3.00 (m, 2H), 2.66 (m, 2H).

Workup

  1. washwashed with 1N HCl (3×50 mL) and brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography on silica gel with 9:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-491c6643125e4f2f904905aa94b316fa
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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