Water → HCID 18407039, compound

HRID 1016641Notes

Reaction equation

HRID 1016641 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([C:24]([CH:34]=O)=[C:25]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[N:26]=2)[CH:23]=1.O>COCCOC>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([C:24](/[CH:34]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:25]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[N:26]=2)[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydride2×HCID 2757432HCID 2757432, compound

Product 1

HCID 18407039HCID 18407039, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Ethyl (diethoxyphosphinyl)acetate (0.44 mL, 0.50 g, 2.2 mmol) was added dropwise to a suspension of sodium hydride (60% in mineral oil, 98 mg, 2.5 mmol) in 1,2-dimethoxyethane (10 mL) and the mixture was stirred at room temperature for 1 h. A suspension of 6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-carboxaldehyde (Description 18, 650 mg, 2.2 mmol) in 1,2-dimethoxyethane (10 mL) was added and the mixture was stirred at room temperature for 1 h. Further sodium hydride (60% in mineral oil, 98 mg, 2.5 mmol) was added and the mixture was stirred at room temperature for 2 h. Water (100 mL) was added and the solid was collected. Toluene was added and evaporated under reduced pressure and the residue was dried in vacuo to give the title compound as a pale brown solid (380 mg, 47%). 1H NMR (360 MHz, CDCl3) δ 8.47 (1H, d, J 1.8 Hz), 7.94 (1H, d, J 16.4 Hz), 7.68 (3H, m), 7.48 (2H, d, J 8.4 Hz), 7.34 (1H, dd, J 9.4, 1.8 Hz), 6.37 (1H, d, J 16.4 Hz), 4.30 (2H, q, J 7.1 Hz), and 1.36 (3H, t, J 7.1 Hz).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 1 h
  3. stirringthe mixture was stirred at room temperature for 2 h
  4. customthe solid was collected
  5. additionToluene was added
  6. customevaporated under reduced pressure
  7. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-6cdef8232d544c21ba80d49dd46b12f4
Source dataset
uspto-grants-2002_11
Patent number
US06476045B2

Reaction notes

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