Triethylamine → HCID 59676053, compound

HRID 642761Notes

Reaction equation

HRID 642761 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]CN(CC)CC.[C:27]([C:31]([C:34]([C:37]([S:40](F)(=[O:42])=[O:41])([F:39])[F:38])([F:36])[F:35])([F:33])[F:32])([F:30])([F:29])[F:28].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH3:20][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:40]([C:37]([F:39])([F:38])[C:34]([F:36])([F:35])[C:31]([F:33])([F:32])[C:27]([F:30])([F:29])[F:28])(=[O:42])=[O:41])[CH:3]=2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 516892Sodium BicarbonateHCID 67239678HCID 67239678, compound

Product 1

HCID 59676053HCID 59676053, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 8-methyl-6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-8-ol (180 mg, 0.711 mmol) in CH2Cl2 (20 mL), Et3N (129 μL, 0.924 mmol) was added dropwise followed by CF3(CF2)3SO2F (153 μL, 0.853 mmol) at 0° C. The reaction mixture was slowly warmed up to 25° C. over 2 hours. Then CH2Cl2, water, and saturated aqueous NaHCO3 solution were added to the mixture. The aqueous layer was extracted with CH2Cl2 and the organic layers were washed with brine, dried, and concentrated. Flash chromatography purification (12% EtOAc/Hexane) was used to yield the title as a white solid.

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2
  2. washthe organic layers were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customFlash chromatography purification (12% EtOAc/Hexane)
  6. customto yield the title as a white solid

Sources & evidence

ORD record
ord-1e8eb6504a0b4a359e5cb8b4fb54588f
Source dataset
uspto-grants-2010_04
Patent number
US07696239B2

Reaction notes

Loading…