Tetrahydrofuran → 3-Fluoro-4-(5-(1-phenylcyclopent-3-enyl)-thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

HRID 1177427Notes

Reaction equation

HRID 1177427 reaction equation
[O:1]1CCCO[CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([C:22]2([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:26][CH:25]=[CH:24][CH2:23]2)[N:16]=3)=[C:9]([F:33])[CH:8]=1.C1COCC1.[OH-].[Na+]>CC(=O)OCC>[F:33][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[C:13]1[S:14][C:15]2[C:20]([N:21]=1)=[CH:19][CH:18]=[C:17]([C:22]1([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:23][CH:24]=[CH:25][CH2:26]1)[N:16]=2)[CH:2]=[O:1]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 671118212-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclopent-3-enyl)thiazolo[5,4-b]pyridine

Product 1

HCID 866387083-Fluoro-4-(5-(1-phenylcyclopent-3-enyl)-thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclopent-3-enyl)-thiazolo[5,4-b]pyridine (0.550 g, 1.20 mmol) in 8 mL 1:1 THF/5N HCl was heated to 70° C. in a sealed vial. After 30 min, the reaction mixture was cooled, treated with ice, 10N NaOH until basic, and EA. The organic layer was washed with water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 3-fluoro-4-(5-(1-phenylcyclopent-3-enyl)-thiazolo[5,4-b]pyridine-2-yl)benzaldehyde which was used without further purification. MS (ESI) m/z: Calculated: 400.1; Observed: 401.1 (M++1).

Workup

  1. temperaturethe reaction mixture was cooled
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3d08c593e9e40dfade20b69ca286b62
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

Loading…