Imidazole → Pyridine, 2-(1,1-difluoro-2-iodoethyl)-5-methyl-

HRID 1987047Notes

Reaction equation

[F:1][C:2]([F:12])([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][N:6]=1)[CH2:3]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:37]I>CC#N.C1(C)C=CC=CC=1>[F:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][N:6]=1)([F:12])[CH2:3][I:37]

Participants

Conditions

Temperature: 90 °C

Procedure

2,2-Difluoro-2-(5-methyl-pyridin-2-yl)-ethanol (8.5 g, 0.05 mol), as prepared in the previous step, was dissolved into toluene:CH3CN (98 mL, 2:1) and cooled to 0° C. To this solution was added PPh3 (19.3 g, 0.074 mol, 1.5×), imidazole (6.7 g, 0.098 mol, 2×) and I2 (18.7 g, 0.074 mol, 1.5×). The reaction was heated to 90° C., then was cooled to RT and concentrated in vacuo to afford a thick amber oil. Purification via flash chromatography (CH2Cl2) afforded the product as a clear oil (4.6 g, 0.016 mol, 33% yield). 1H NMR (300 Hz, CDCl3) δ 8.48 (s, 1H), 7.61 (m, 1H), 3.92 (t, J=14.7 Hz), 2.41 (s, 3H); LC/MS (m/z) [M+1]+ 284.1 (calculated for C8H9F2IN, 284.07).

Workup

temperaturewas cooled to RT
concentrationconcentrated in vacuo
customto afford a thick amber oil
customPurification via flash chromatography (CH2Cl2)

Sources & evidence

ORD record: ord-6b168de3eefe4c0a9f716c8a5dd696d2
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550474B2

Reaction notes

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