2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridine → 4-(5-Chlorothiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzaldehyde

HRID 1177407Notes

Reaction equation

HRID 1177407 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]([Cl:22])[N:16]=3)=[C:9]([F:23])[CH:8]=1>C1COCC1>[Cl:22][C:17]1[N:16]=[C:15]2[S:14][C:13]([C:10]3[CH:11]=[CH:12][C:7]([CH:2]=[O:1])=[CH:8][C:9]=3[F:23])=[N:21][C:20]2=[CH:19][CH:18]=1

Participants

3

Reactant 1

HCID 591748622-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridine

Product 1

HCID 866387064-(5-Chlorothiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-chlorothiazolo[5,4-b]pyridine (5.00 g, 14.3 mmol) in 100 mL 1:1 THF/5N aq. HCl was heated in a sealed tube to 70° C. The thick orange mixture was cooled slightly and an additional 50 mL THF was added. The reaction mixture was sealed and heating continued. After 2 h, the reaction mixture was cooled and allowed to stir 3 days at ambient temperature. The reaction mixture was cooled and THF was removed in vacuo. The resulting yellow solid was collected by filtration through a frit, rinsing with water. The material was dried on the frit for several hours and dried in vacuo overnight to give 4-(5-chlorothiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzaldehyde as a light yellow/orange solid. MS (ESI) m/z: calculated: 292.0: Observed: 292.9 (M++1).

Workup

  1. temperatureThe thick orange mixture was cooled slightly
  2. customThe reaction mixture was sealed
  3. temperatureheating
  4. temperaturethe reaction mixture was cooled
  5. temperatureThe reaction mixture was cooled
  6. customTHF was removed in vacuo
  7. filtrationThe resulting yellow solid was collected by filtration through a frit
  8. washrinsing with water
  9. customThe material was dried on the frit for several hours
  10. customdried in vacuo overnight

Sources & evidence

ORD record
ord-f07e74219b434edabedb5ea03b906bcb
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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