Hydrogen Bromide → HCID 11952365, compound

HRID 1669104Notes

Reaction equation

HRID 1669104 reaction equation
N([O-])=O.[Na+].N[C:6]1[N:7]=[N+:8]([O-:21])[C:9]2[CH:18]=[C:17]3[C:13]([CH2:14][CH:15]([CH2:19][OH:20])[CH2:16]3)=[CH:12][C:10]=2[N:11]=1.[BrH:22].CN(C=O)C>CCOC(C)=O>[Br:22][C:6]1[N:7]=[N+:8]([O-:21])[C:9]2[CH:18]=[C:17]3[C:13]([CH2:14][CH:15]([CH2:19][OH:20])[CH2:16]3)=[CH:12][C:10]=2[N:11]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 6228DimethylformamideHCID 11952364HCID 11952364, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 11952365HCID 11952365, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

NaNO2 (23 mg, 0.33 mmol) was added to a stirred mixture of amine 124 (77 mg, 0.33 mmol), HBr (48%, 2 mL) and DMF (2 mL) at 20° C. and the mixture stirred at 20° C. for 1 h. CuBr (57 mg, 0.40 mmol) was added and the reaction mixture stirred at 20° C. for 90 min. The mixture was diluted with EtOAc (50 mL) and washed with water (3×20 mL). The organic solution was dried and the solvent evaporated to give an orange oil, that was purified by chromatography, eluting with a gradient (0-30%) of EtOAc/pet. ether, to give bromide 125 (40 mg, 41%) as an oil: 1H NMR δ 8.19 (s, 1H, H-9), 7.74 (s, 1H, H-5), 3.72 (d, J=6.5 Hz, 2H, CH2O), 3.22-3.33 (m, 2H, CH2), 2.96-3.08 (m, 2H, CH2), 2.80-2.89 (m, 1H, CH), OH not observed; HRMS calcd for C11H1079BrN3O2 (M+) m/z 294.9956, found 294.9949; calcd for C11H1081BrN3O2 (M+) m/z 296.9936, found 296.9943.

Workup

  1. stirringthe reaction mixture stirred at 20° C. for 90 min
  2. washwashed with water (3×20 mL)
  3. customThe organic solution was dried
  4. customthe solvent evaporated
  5. customto give an orange oil, that
  6. customwas purified by chromatography
  7. washeluting with a gradient (0-30%) of EtOAc/pet. ether

Sources & evidence

ORD record
ord-7b80a8e731cb4e17b3c2f3452889ca30
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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