Dimethylformamide → HCID 59680142, compound

HRID 416658Notes

Reaction equation

HRID 416658 reaction equation
O=P(Cl)(Cl)Cl.[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:16]=[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]2[CH:23]=1)([O-:8])=[O:7].CN([CH:27]=[O:28])C>[OH-].[Na+]>[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:16]=[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]2[C:23]=1[CH:27]=[O:28])([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 6228Dimethylformamide3×HCID 24813Phosphorus oxychloride2×HCID 596799982-(2-Nitrophenyl)imidazo[1,2-a]pyridine

Product 1

HCID 59680142HCID 59680142, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

In a dry flask charged with DMF (2.7 g, 37 mmol) and cooled to 0° C. was added slowly POCl3 over 5 minutes. The solution was stirred for 10 min at 0° C. was warmed to room temperature over 1 hour. To the deep red color solution recooled to 0° C. was added 2-(2-Nitro-phenyl)-imidazo[1,2-a]pyridine (1.0 g, 4.18 mmol) in DMF (8 ml). The reaction was stirred for 5.5 hours; LC-MS indicated some product formation. A second addition of the Vilsmeier complex (from 2.7 g of DMF and 1.47 g POCl3) was charged and the reaction stirred overnight, then heated to 50° C. for 3 hours until reaction completion. The reaction was cooled to room temperature, poured onto ice, adjusted to pH=7 with IN NaOH. The product was extracted into CH2Cl2 (3×50 ml), washed with brine, dried over Na2SO4 and concentrated to obtain the product as a white solid (1.03 g, 92% yield). (MS, M++H=268.0)

Workup

  1. temperaturewas warmed to room temperature over 1 hour
  2. customrecooled to 0° C.
  3. stirringThe reaction was stirred for 5.5 hours
  4. additionwas charged
  5. stirringthe reaction stirred overnight
  6. temperatureheated to 50° C. for 3 hours until reaction completion
  7. temperatureThe reaction was cooled to room temperature
  8. additionpoured onto ice
  9. extractionThe product was extracted into CH2Cl2 (3×50 ml)
  10. washwashed with brine
  11. dry with materialdried over Na2SO4
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-426e3a5d1d034a8ebd789d51a132728d
Source dataset
uspto-grants-2012_01
Patent number
US08088928B2

Reaction notes

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