Chloroacetaldehyde → HCID 46913420, compound

HRID 1025387Notes

Reaction equation

HRID 1025387 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.N[C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][N:13]=1.ClC[CH:21]=[O:22].O.C[CH2:25][OH:26]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:17]3[CH:12]=[N:13][C:14]([O:22][CH3:21])=[C:15]([O:26][CH3:25])[CH:16]=3)=[CH:9][N:10]=2)[CH:7]=1

Participants

6

Reactant 5

HCID 33ChloroacetaldehydeHCID 702EthanolHCID 962WaterHCID 706222-Amino-5-bromopyridineHCID 27955476-Bromoimidazo[1,2-a]pyridine

Product 1

HCID 46913420HCID 46913420, compound

Conditions

Temperature
100 °C

Procedure

6-bromoimidazo[1,2-a]pyridine. To a 100 mL round-bottomed flask was added 2-amino-5-bromopyridine (5.04 g, 29.1 mmol), chloroacetaldehyde, approx. 50 wt. % solution in water (18.74 mL, 146 mmol), and EtOH (25 mL). The resulting reaction mixture was heated at 100° C. under N2 for 4 h. The reaction was cooled to rt. Solvent was concentrated. The residue was redissolved in EtOAc. The organic layer was washed with sat. NaHCO3 (2×40 mL), water (2×40 mL), brine, dried over MgSO4 and removed solvent. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, 120 g SiO2, DCM:MeOH=96%:4% to DCM:MeOH (2M NH3)=95%:5%, Flow=85 mL/min). Solvent was removed in vacuo to afford the desired product as brown solid (5.0 g). MS (ESI pos. ion) m/z: 196.9. Calcd exact mass for C7H5BrN2: 195.9. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.24 (d, J=9.65 Hz, 1H) 7.54 (d, J=9.65 Hz, 1H) 7.57 (s, 1H) 7.65 (s, 1H) 8.30 (s, 1H).

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe reaction was cooled to rt
  3. concentrationSolvent was concentrated
  4. dissolutionThe residue was redissolved in EtOAc
  5. washThe organic layer was washed with sat. NaHCO3 (2×40 mL), water (2×40 mL), brine
  6. dry with materialdried over MgSO4
  7. customremoved solvent
  8. customThe crude product was purified
  9. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-66bcb2a5ec3a41319c6b885874fe201e
Source dataset
uspto-grants-2014_05
Patent number
US08729074B2

Reaction notes

Loading…