Dichloromethane → HCID 59174916, compound

HRID 1177394Notes

Reaction equation

HRID 1177394 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1[CH:25]=[C:26]([CH:48]([OH:50])[CH3:49])[CH:27]=[CH:28][C:29]=1[C:30]1[S:31][C:32]2[C:37]([N:38]=1)=[CH:36][CH:35]=[C:34]([C:39]1([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:41][CH2:40]1)[N:33]=2.ClCCl.C([O-])(O)=O.[Na+]>>[F:23][C:24]1[CH:25]=[C:26]([C:48](=[O:50])[CH3:49])[CH:27]=[CH:28][C:29]=1[C:30]1[S:31][C:32]2[C:37]([N:38]=1)=[CH:36][CH:35]=[C:34]([C:39]1([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH2:40][CH2:41]1)[N:33]=2

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67111620HCID 67111620, compound

Product 1

HCID 59174916HCID 59174916, compound

Procedure

Dess-Martin periodinane (0.266 g, 0.627 mmol) was added to a solution of 1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)ethanol (0.204 g, 0.522 mmol) in dichloromethane (15.00 mL, 0.522 mmol), and the reaction mixture was stirred at ambient temperature for 65 min. Saturated aqueous NaHCO3 was added and the reaction stirred for 5 min. The organic layer was dried and concentrated in vacuo, and purified by silica gel chromatography: ISCO 40 g column, 20-40% (3% Et3N in EtOAc)/hexanes to give 1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)ethanone. MS (ESI) m/z: Calculated: 388.1; Observed: 389.0 (M++1).

Workup

  1. stirringthe reaction stirred for 5 min
  2. customThe organic layer was dried
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-6a97f21afb17475689690e43263de2d7
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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