HCID 86669017, compound → HCID 86723323, compound

HRID 2366288Notes

Reaction equation

HRID 2366288 reaction equation
[Cl:1][C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([N+:17]([O-])=O)=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:20])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1>CC(O)=O.[Fe]>[Cl:20][C:12]1[C:11]([C:9]2[S:8][C:7]3[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][C:6]=3[N:10]=2)=[C:16]([NH2:17])[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 86669017HCID 86669017, compound

Product 1

HCID 86723323HCID 86723323, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Iron powder (6.08 g, 109 mmol) was added to a solution of 4-chloro-2-(2-chloro-6-nitrophenyl)thiazolo[5,4-c]pyridine (3.55 g, 10.9 mmol) in AcOH (100 mL). The reaction mixture was heated at 100° C. for 30 minutes and then allowed to cool to room temperature. The volatiles were removed under reduced pressure and the resultant residue was dissolved in DCM/MeOH and filtered through Celite® washing further with MeOH. The combined washings were concentrated under reduced pressure and the resultant residue was triturated with 10% MeOH in DCM to afford the title compound as an orange/red solid (2.55 g, 79% yield). 1H NMR (400 MHz, CDCl3): δ 8.44 (d, J=5.6 Hz, 1H), 7.83 (d, J=5.7 Hz, 1H), 7.16 (t, J=7.9 Hz, 1H), 6.89 (dd, J=1.2, 7.8 Hz, 1H), 6.73 (dd, J=1.2, 8.3 Hz, 1H), 6.14 (br s, 2H).

Workup

  1. temperatureto cool to room temperature
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionthe resultant residue was dissolved in DCM/MeOH
  4. filtrationfiltered through Celite®
  5. washwashing further with MeOH
  6. concentrationThe combined washings were concentrated under reduced pressure
  7. customthe resultant residue was triturated with 10% MeOH in DCM

Sources & evidence

ORD record
ord-40cfc784072342a7bfaaab72a89428de
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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