Pyridine → HCID 59676124, compound

HRID 624478Notes

Reaction equation

HRID 624478 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

Conditions

Temperature
25 °C

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-8d00c43252db4238b5f36b0f4c93983c
Source dataset
uspto-grants-2016_04
Patent number
US09303037B2

Reaction notes

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