Iodine chloride → HCID 58266297, compound

HRID 60313Notes

Reaction equation

HRID 60313 reaction equation
[I:1]Cl.[Br:3][C:4]1[N:12]=[CH:11][C:10]2[NH:9][C:8]3[N:13]=[CH:14][CH:15]=[CH:16][C:7]=3[C:6]=2[CH:5]=1.C([O-])(=O)C.[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(O)(=O)C>[Br:3][C:4]1[N:12]=[CH:11][C:10]2[NH:9][C:8]3[N:13]=[CH:14][C:15]([I:1])=[CH:16][C:7]=3[C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 656671Sodium PyrosulfiteHCID 582667276-Bromo-9H-pyrrolo[2,3-b:5,4-c′]dipyridine

Product 1

HCID 58266297HCID 58266297, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of iodine monochloride (32.5 g, 200 mmol) in acetic acid (120 mL) was added portionwise over 2 h to a mixture of 6-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (5.0 g, 20 mmol) and sodium acetate (18.2 g, 221 mmol) in acetic acid (120 mL) at 100° C. The reaction mixture was cooled to ambient temperature and poured into saturated sodium metabisulfite solution (20% w/w, 400 mL). The resultant precipitate was collected by filtration and the solid was washed with water (50 mL) and diethyl ether (2×50 mL) then dried at 45° C. until constant weight was achieved, to afford the title compound as a grey solid (6.3 g, 83%). 1H NMR (DMSO-D6, 300 MHz) 12.49 (s, 1H); 9.14 (d, J=2.1 Hz, 1H); 8.79 (d, J=2.1 Hz, 1H); 8.71 (s, 1H); 8.49 (s, 1H). LCMS (Method B): RT=3.40 min, M+H+=374/376.

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. washthe solid was washed with water (50 mL) and diethyl ether (2×50 mL)
  3. customthen dried at 45° C. until constant weight

Sources & evidence

ORD record
ord-95acc7fd569241d6829c8f213154a520
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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