Acetic Acid → HCID 86662416, compound

HRID 389529Notes

Reaction equation

HRID 389529 reaction equation
[F:1][C:2]([F:17])([F:16])[S:3]([O:6][C:7]1[CH:8]=[C:9]2[CH:15]=[CH:14][S:13][C:10]2=[CH:11][N:12]=1)(=[O:5])=[O:4].C([O-])(=O)C.[Na+].[Br:23]Br.CC(O)=O.C([O-])([O-])=O.[Na+].[Na+]>>[F:17][C:2]([F:1])([F:16])[S:3]([O:6][C:7]1[CH:8]=[C:9]2[C:15]([Br:23])=[CH:14][S:13][C:10]2=[CH:11][N:12]=1)(=[O:5])=[O:4]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 24408BromineHCID 517045Sodium AcetateHCID 87138463HCID 87138463, compound

Product 1

HCID 86662416HCID 86662416, compoundYield 55%

Conditions

Temperature
90 °C

Procedure

A sealable vial was charged with thieno[2,3-c]pyridin-5-yl trifluoromethanesulfonate (109 mg, 0.300 mmol), sodium acetate (75.3 mg, 0.900 mmol) and 1.0 M bromine in AcOH (0.900 mL, 0.900 mmol). The reaction was heated in a microwave reactor at 90° C. for 2 h. The reaction mixture was treated with aqueous Na2CO3 until the pH was >9, then extracted with EtOAc (3×20 mL). The combined extracts were washed with water (10 mL) and brine (10 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by ISCO chromatography (0 to 25% EtOAc:heptane) to afford 60 mg (55%) of the title compound as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.26 (d, J=0.4 Hz, 1 H), 8.61 (s, 1 H), 7.92 (d, J=1.2 Hz, 1H); MS (ESI): 362.08, 384.04 [M+H]+; HPLC tR=4.39 min (ZQ3: polar—5 min).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined extracts were washed with water (10 mL) and brine (10 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by ISCO chromatography (0 to 25% EtOAc:heptane)

Sources & evidence

ORD record
ord-575300b06dad4d58a95fbf55ae63e5a7
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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