Diethyl Ether → 8-bromo-5-methyl-2,3,5,6-tetrahydropyrido[2,3-b][1,5]diazocin-4(1H)-one

HRID 1880009Notes

Reaction equation

HRID 1880009 reaction equation
[Br:1]Br.[CH3:3][N:4]1[C:11](=[O:12])[CH2:10][CH2:9][NH:8][C:7]2[N:13]=[CH:14][CH:15]=[CH:16][C:6]=2[CH2:5]1.C(OCC)C>C(O)(=O)C>[Br:1][C:15]1[CH:14]=[N:13][C:7]2[NH:8][CH2:9][CH2:10][C:11](=[O:12])[N:4]([CH3:3])[CH2:5][C:6]=2[CH:16]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 593328875-Methyl-2,3,5,6-tetrahydropyrido[2,3-b][1,5]diazocin-4(1h)-one

Product 1

HCID 593328748-bromo-5-methyl-2,3,5,6-tetrahydropyrido[2,3-b][1,5]diazocin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (189 μL, 3.7 mmol) was added to a solution of 5-methyl-2,3,5,6-tetrahydropyrido[2,3-b][1,5]diazocin-4(1H)-one (460 mg, 2.4 mmol) in 10 mL of acetic acid and stirred at room temperature for 17 h. Add 30 mL of diethyl ether and collect orange solid product via suction filtration. Redissolve the solid in DCM and wash with NaHCO3, dry the organic layer over MgSO4, and concentrate in vacuo to obtain orange solid product. Yield 670 mg (quant); 1H NMR (400 MHz, CDCl3) δ 8.10 (d, J=2.0 Hz, 1H), 7.50 (d, J=2.4 Hz, 1H), 5.17 (bs, 1H), 4.49 (s, 2H), 3.59 (bm, 2H), 3.04 (t, J=6.8 Hz, 2H), 2.85 (s, 3H); ESI MS m/z 270, 272 [C10H12N3OBr+H]+

Workup

  1. customcollect orange solid product
  2. filtrationvia suction filtration
  3. dissolutionRedissolve the solid in DCM
  4. washwash with NaHCO3
  5. dry with materialdry the organic layer over MgSO4
  6. concentrationconcentrate in vacuo
  7. customto obtain orange solid product

Sources & evidence

ORD record
ord-fcec3cbb3acc44a7a1180bb3039d2011
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

Loading…