Benzenesulfonyl chloride → HCID 68323881, compound

HRID 573572Notes

Reaction equation

HRID 573572 reaction equation
[Br:1][C:2]1[S:12][C:5]2[N:6]=[C:7]([CH3:11])[CH:8]=[C:9]([NH2:10])[C:4]=2[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1.CC(C)([O-])C.[Na+].[C:26]1([S:32](Cl)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.CN(C=O)C>[Br:1][C:2]1[S:12][C:5]2=[N:6][C:7]([CH3:11])=[CH:8][C:9]([NH:10][S:32]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:34])=[O:33])=[C:4]2[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 23676156Sodium t-butoxideHCID 68323876HCID 68323876, compound

Product 1

HCID 68323881HCID 68323881, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-bromo-3-(3-bromophenyl)-6-methylthieno[2,3-b]pyridin-4-amine (Description 49) (1 g, 2.51 mmol) in THF (10 mL) and DMF (5 mL) was added sodium tert-butoxide (0.603 g, 6.28 mmol) and benzenesulfonyl chloride (0.648 mL, 5.02 mmol). The reaction mixture stirred at RT under nitrogen for ca. 30 min. The reaction mixture was quenched with saturated ammonium chloride solution (ca. 30 mL) and extracted with DCM (25 mL×4). The combined organics were dried and concentrated. The residue was purified via normal phase chromatography eluted with a gradient of 0-50% ethyl acetate in DCM, to afford the title compound (1.12 g). LCMS (A) m/z: 539 [M+1]+, Rt 1.45 min (acidic).

Workup

  1. customThe reaction mixture was quenched with saturated ammonium chloride solution (ca. 30 mL)
  2. extractionextracted with DCM (25 mL×4)
  3. customThe combined organics were dried
  4. concentrationconcentrated
  5. customThe residue was purified via normal phase chromatography
  6. washeluted with a gradient of 0-50% ethyl acetate in DCM

Sources & evidence

ORD record
ord-182df79fb3594a85a67fd4afc2117447
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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