Acetic Acid → HCID 58266686, compound

HRID 1506031Notes

Reaction equation

HRID 1506031 reaction equation
[BrH:1].C(O)(=O)C.N[C:7]1[N:15]=[CH:14][C:13]2[NH:12][C:11]3[N:16]=[CH:17][C:18]([Br:20])=[CH:19][C:10]=3[C:9]=2[CH:8]=1.BrBr.N([O-])=O.[Na+].O>[OH-].[NH4+].O.C(Cl)Cl>[Br:20][C:18]1[CH:17]=[N:16][C:11]2[NH:12][C:13]3[CH:14]=[N:15][C:7]([Br:1])=[CH:8][C:9]=3[C:10]=2[CH:19]=1

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 962WaterHCID 24408BromineHCID 23668193Sodium NitriteHCID 58266658HCID 58266658, compound

Product 1

HCID 58266686HCID 58266686, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 86589665Water ammonium hydroxideSolvent

Procedure

A solution of hydrogen bromide (33%) in acetic acid (1.10 mL, 6.08 mmol) was added to 6-amino-3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (80.1 mg, 0.304 mmol) at 0° C. To the resulting suspension was added bromine (18 μL, 0.34 mmol), and then a 1N solution of sodium nitrite in water (0.43 mL, 0.43 mmol), and the mixture was allowed to warm to ambient temperature. After 1 h, the reaction mixture was diluted with concentrated ammonium hydroxide-water (1:1) and DCM, filtered to remove the solid, and the filtrate layers separated. The aqueous phase was extracted into DCM and the combined organic phase was concentrated in vacuo. The residue was purified by flash chromatography (silica, 0-100% ethyl acetate in hexanes).

Workup

  1. filtrationfiltered
  2. customto remove the solid
  3. customthe filtrate layers separated
  4. extractionThe aqueous phase was extracted into DCM
  5. concentrationthe combined organic phase was concentrated in vacuo
  6. customThe residue was purified by flash chromatography (silica, 0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d73c655060dd40f9a9833d4ffc78da3e
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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