Bromine → HCID 59332896, compound

HRID 1880015Notes

Reaction equation

HRID 1880015 reaction equation
[Br:1]Br.[NH:3]1[CH2:10][CH2:9][CH2:8][NH:7][CH2:6][C:5]2[CH:11]=[CH:12][CH:13]=[N:14][C:4]1=2>C(O)(=O)C.C(Cl)Cl>[Br:1][C:12]1[CH:13]=[N:14][C:4]2[NH:3][CH2:10][CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:11]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 59332862HCID 59332862, compound

Product 1

HCID 59332896HCID 59332896, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Bromine (33 μL, 0.63 mmol) was added to a solution of 1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocine (69 mg, 0.42 mmol) in 5 mL of acetic acid and stirred at room temperature for 19 h. Dilute with DCM and wash with saturated NaHCO3, wash the organic layer with brine, separate, dry over MgSO4, and concentrate in vacuo to obtain orange solid product. Yield 91 mg (90%); 1H NMR (400 MHz, CDCl3) δ 8.05 (s, 1H), 7.54 (s, 1H), 4.44 (s, 2H), 3.68 (s, 2H), 3.33 (m, 2H), 2.05 (m, 2H); ESI MS m/z 242, 244 [C9H12N3Br+H]+

Workup

  1. washwash with saturated NaHCO3
  2. washwash the organic layer with brine
  3. customseparate
  4. dry with materialdry over MgSO4
  5. concentrationconcentrate in vacuo
  6. customto obtain orange solid product

Sources & evidence

ORD record
ord-fee23bb66d11445ba024c29dfcc486ec
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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