Diisopropylethylamine → Ethyl 5-[(diethoxyphosphinyl)hydroxymethyl]imidazo[1,2-a]pyridine-2-carboxylate

HRID 861997Notes

Reaction equation

[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].C(N(CC)C(C)C)(C)C.[CH:18]([C:20]1[N:25]2[CH:26]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:28]=[C:24]2[CH:23]=[CH:22][CH:21]=1)=[O:19]>C1(C)C=CC=CC=1>[CH2:3]([O:2][P:1]([CH:18]([OH:19])[C:20]1[N:25]2[CH:26]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:28]=[C:24]2[CH:23]=[CH:22][CH:21]=1)([O:5][CH2:6][CH3:7])=[O:8])[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

Diethyl phosphite (1.7 g, 12.3 mmol, Aldrich), N,N-diisopropylethylamine (1.63 g, 12.4 mmol, Aldrich) and toluene (60 mL) were combined in a 100 mL flask equipped with a N2 inlet and condensor. After warming this solution to 60° C., the product from Example 54 was added. After stirring at 75°-80° C. for 3 h, all solvent was removed from this mixture and the residue was chromatographed (7.5/92.4/0.1 isopropanol/CH2Cl2 /HOAc) to give 1.2 g (66%) of the title product.

Workup

customequipped with a N2 inlet
customall solvent was removed from this mixture
customthe residue was chromatographed (7.5/92.4/0.1 isopropanol/CH2Cl2 /HOAc)

Sources & evidence

ORD record: ord-53c716aaa28b41adac3665b2d0444bf6
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05716964

Reaction notes

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