Anisole → 5-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridine-4-thiol

HRID 911058Notes

Reaction equation

HRID 911058 reaction equation
COC1C=CC(C[S:8][C:9]2[C:14]([Br:15])=[CH:13][N:12]=[C:11]([NH:16][C:17]3[S:18][CH:19]=[C:20]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:21]=3)[CH:10]=2)=CC=1.C1(OC)C=CC=CC=1.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[Br:15][C:14]1[C:9]([SH:8])=[CH:10][C:11]([NH:16][C:17]2[S:18][CH:19]=[C:20]([CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:21]=2)=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 866347724-(4-methoxybenzylthio)-5-bromo-N-(4-phenethylthiazol-2-yl)pyridine-2-amine

Product 1

HCID 1785277275-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridine-4-thiolYield 72.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
75 °C

Procedure

4-(4-methoxybenzylthio)-5-bromo-N-(4-phenethylthiazol-2-yl)pyridine-2-amine (1.23 g, 2.4 mmol) was dissolved in TFA (10 mL):anisole (2 mL) (5:1). The reaction mixture was stirred at 75° C. overnight, then neutralized with solid NaHCO3, extracted with EtOAc, dried, and concentrated. The crude material was triturated in MeOH and filtered. The filtrate was further concentrated and triturated again with MeOH. The solids were combined and dried to give the desired product (0.68 g, 72% yield).

Workup

  1. extractionextracted with EtOAc
  2. customdried
  3. concentrationconcentrated
  4. customThe crude material was triturated in MeOH
  5. filtrationfiltered
  6. concentrationThe filtrate was further concentrated
  7. customtriturated again with MeOH
  8. customdried

Sources & evidence

ORD record
ord-a0b7f573027c4478b41296cc46429dfd
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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