Tetrahydrofuran → HCID 57845127, compound

HRID 734314Notes

Reaction equation

HRID 734314 reaction equation
[Br:1][C:2]1[C:6]2[C:7](=[O:11])[NH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.C1C(=O)N([I:19])C(=O)C1.C1COCC1.[O-]S([O-])=O.[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[C:6]2[C:7](=[O:11])[NH:8][CH:9]=[C:10]([I:19])[C:5]=2[S:4][CH:3]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 120273N-IodosuccinimideHCID 184507963-Bromothieno[3,2-c]pyridin-4(5H)-one

Product 1

HCID 57845127HCID 57845127, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of compound 10 (see Example 4(c)) (1.9 g, 8.3 mmol) and N-iodosuccimide (NIS, 2.2 g, 49.9 mmol) in DMF (25 ml) and THF (20 ml) was stirred for 5 hours at 40° C. The reaction mixture was poured into 10% Na2SO3 and ethyl acetate. The insoluble product was collected by filtration, washed with ethyl acetate and dried under reduced pressure to give 3-bromo-7-iodo-5H-thieno[3,2-c]pyridin-4-one (990 mg). The filtrate was collected, dried over Na2SO4, filtered and concentrated in vacuo. The generated precipitate was washed with MeOH to further yield 3-bromo-7-iodo-5H-thieno[3,2-c]pyridin-4-one (1.1 g). 1H NMR (400 MHz, DMSO-d6) ppm 11.75 (s, 1H), 7.79 (s, 1H), 7.57 (s, 1H).

Workup

  1. filtrationThe insoluble product was collected by filtration
  2. washwashed with ethyl acetate
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-1ca07353cebc4c92b0524f23949653c1
Source dataset
uspto-grants-2009_09
Patent number
US07592352B2

Reaction notes

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