Water → HCID 86728276, compound

HRID 1776885Notes

Reaction equation

HRID 1776885 reaction equation
O=P(Cl)(Cl)Cl.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]([C:13]2[N:14]=[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]3[CH:21]=2)[CH:12]=1.O.CN([CH:28]=[O:29])C>>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]([C:13]2[N:14]=[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]3[C:21]=2[CH:28]=[O:29])[CH:12]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 71295498HCID 71295498, compound

Product 1

HCID 86728276HCID 86728276, compoundYield 90%

Conditions

Temperature
25 °C

Procedure

POCl3 (0.39 g, 2.5 mmol) was added to DMF (0.43 g, 6 mmol) by dropwise at 0° C. Then 2-(5-bromo-2-methoxyphenyl)imidazo[1,2-a]pyridine (0.1 g, 0.33 mmol) in DMF (3 mL) was added. Then warmed to 25° C. and heated to 120° C. and stirred for 30 minutes and at 80° C. for 2 hours and then cooled to 25° C. H2O (20 mL) was added and extracted with EtOAc (3*50 mL), washed by aq NaHCO3 (3*50 mL) and brine (50 mL). After concentrated, the resulting residue was purified using prep-TLC (petroleum ether:EtOAc=3:1) to provide 2-(5-bromo-2-methoxyphenyl)imidazo[1,2-a]pyridine-3-carbaldehyde (100 mg, yield: 90%). 1H-NMR (CDCl3, 400 MHz) δ 9.85 (s, 1H), 9.60 (s, 1H), 7.77˜7.81 (m, 2H), 7.54˜7.58 (m, 2H), 7.12˜7.15 (m, 1H), 6.92˜6.94 (m, 1H), 3.82 (s, 3H). MS (M+H)+: 331/333.

Workup

  1. temperatureheated to 120° C.
  2. temperaturecooled to 25° C
  3. extractionextracted with EtOAc (3*50 mL)
  4. washwashed by aq NaHCO3 (3*50 mL) and brine (50 mL)
  5. concentrationAfter concentrated
  6. customthe resulting residue was purified

Sources & evidence

ORD record
ord-aa38ac95020248bb92ba3a9c161a664d
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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