Dichloromethane → HCID 68635025, compound

HRID 1177490Notes

Reaction equation

HRID 1177490 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:51])[CH2:49][CH3:50])[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:51])[CH2:49][CH3:50])[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 68635762HCID 68635762, compound

Product 1

HCID 68635025HCID 68635025, compound

Procedure

Dess-Martin periodinane (0.524 g, 1.24 mmol) was added to a solution of 1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)propan-1-ol (0.500 g, 1.24 mmol) in dichloromethane (25.00 ml, 1.24 mmol), and the reaction was stirred at ambient temperature for 60 min. Saturated aq. NaHCO3 was added and the reaction stirred for 5 min. The organic layer was dried, filtered, and concentrated in vacuo and the residue purified by silica gel chromatography: ISCO 120 g column, 20-30% (3% Et3N in EtOAc)/Hex to give 1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)propan-1-one. MS (ESI) m/z: Calculated: 402.1; Observed: 403.0 (M++H).

Workup

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

Sources & evidence

ORD record
ord-876d2a318379400aa04b15e9e10174a1
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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