Pyridine → HCID 59676124, compound

HRID 2040458Notes

Reaction equation

HRID 2040458 reaction equation
C[C:2]1([OH:19])[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[C:9]4[CH:15]=[CH:16][CH:17]=[CH:18][C:8]=4[S:7][CH2:6][C:5]=3[C:4]=2[CH2:3]1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].N1C=CC=C[CH:26]=1>C(Cl)Cl>[CH3:26][N:11]1[C:10]2[C:9]3[CH:15]=[CH:16][CH:17]=[CH:18][C:8]=3[S:7][CH2:6][C:5]=2[C:4]2[C:12]1=[CH:13][CH:14]=[C:2]([O:19][S:21]([CH3:20])(=[O:23])=[O:22])[CH:3]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67239678HCID 67239678, compound

Product 1

HCID 59676124HCID 59676124, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-methyl-6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-8-ol (35, mg, 0.131 mmol), CH3SO2Cl (15 μL, 0.197 mmol, 1.5 eq.), pyridine (20 mg, 0.262 mmol, 2.0 eq.) in CH2Cl2 (1 mL) was stirred at 25° C. for 2 hours. The mixture was then partitioned between CH2Cl2 and saturated NaHCO3 aqueous solution. The aqueous layer was extracted three times with CH2Cl2. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to yield crude material. The crude material was purified by chromatography to yield the title compound as a white solid.

Workup

  1. customThe mixture was then partitioned between CH2Cl2 and saturated NaHCO3 aqueous solution
  2. extractionThe aqueous layer was extracted three times with CH2Cl2
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield crude material
  8. customThe crude material was purified by chromatography

Sources & evidence

ORD record
ord-0950acf653b440c2a4c631180e6a4d96
Source dataset
uspto-grants-2013_11
Patent number
US08580840B2

Reaction notes

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