Acetic Acid → HCID 86681210, compound

HRID 1848238Notes

Reaction equation

HRID 1848238 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([N:11]([CH2:14][C:15]2[CH:25]=[CH:24][C:18]3[N:19]=[C:20]([S:22][CH3:23])[S:21][C:17]=3[CH:16]=2)[CH:12]=O)=[C:4]([F:26])[CH:3]=1.CC(O)=O>[Fe].CCO>[Br:1][C:2]1[CH:3]=[C:4]([F:26])[C:5]2[N:11]([CH2:14][C:15]3[CH:25]=[CH:24][C:18]4[N:19]=[C:20]([S:22][CH3:23])[S:21][C:17]=4[CH:16]=3)[CH:12]=[N:8][C:6]=2[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86681209HCID 86681209, compound

Product 1

HCID 86681210HCID 86681210, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of N-(4-bromo-2-fluoro-6-nitrophenyl)-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)formamide (4.8 g, 10.55 mmol) from the previous step, HOAc (15 mL) and EtOH (50 mL) at rt was added portionwise iron powder (1.77 g, 31.65 mmol). The mixture was heated at 80° C. for 2.5 h. After cooling to rt, the mixture was partitioned between saturated aq NaHCO3 and a 10:1 mixture of EtOAc and MeOH. The biphasic mixture was filtered through Celite, and the layers of the filtrate were separated. The aqueous layer was extracted with a 10:1 mixture of EtOAc and MeOH. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residual solid was purified by trituration with diethyl ether to afford 6-((5-bromo-7-fluoro-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole (1.39 mg, 39%) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.56 (s, 1H), 7.87 (m, 1H), 7.80 (d, J=8.4 Hz, 1H), 7.75 (m, 1H), 7.30-7.34 (m, 2H), 5.66 (s, 2H), 2.76 (s, 3H); LCMS (ESI) m/z 408 and 410 (M+H)+.

Workup

  1. temperatureAfter cooling to rt
  2. customthe mixture was partitioned between saturated aq NaHCO3
  3. additiona 10:1 mixture of EtOAc and MeOH
  4. filtrationThe biphasic mixture was filtered through Celite
  5. customthe layers of the filtrate were separated
  6. extractionThe aqueous layer was extracted with a 10:1 mixture of EtOAc and MeOH
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residual solid was purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-8f7e9c80ed2d4615bb9504e385e3646d
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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