Diiodomethane → 5-iodo-1-isobutyl-1H-imidazole-4-carbonitrile

HRID 574013Notes

Reaction equation

N[C:2]1[N:6]([CH2:7][CH:8]([CH3:10])[CH3:9])[CH:5]=[N:4][C:3]=1[C:11]#[N:12].C(I)[I:14].C(ON=O)CC(C)C>C(Cl)(Cl)Cl>[I:14][C:2]1[N:6]([CH2:7][CH:8]([CH3:10])[CH3:9])[CH:5]=[N:4][C:3]=1[C:11]#[N:12]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-amino-1-isobutyl-1H-imidazole-4-carbonitrile S10 (410 mg, 2.5 mmol, 1 equiv) and CH2I2 (2 mL) in CHCl3 (25 mL) at 80° C. was added a solution of isoamylnitrite (1.36 mL, 10.2 mmol, 4.0 equiv) in CHCl3 (5.0 mL) over 20 min. The reaction was heated for additional 30 min, then cooled to 25° C. and concentrated in vacuo. Purification by silica gel column chromatography (1/9 EtOAc/hexanes-7/3 EtOAc/hexanes, gradient) afforded the title compound (536 mg, 78%) as an orange solid: 1H NMR (CDCl3, 600 Hz) δ 0.92 (d, J=7.2 Hz, 6H), 2.12 (non, J=10.2 Hz, 1H), 3.76 (d, J=7.8 Hz, 2H), 7.62 (s, 1H); 13C NMR (CDCl3, 150 Hz) δ 19.6, 29.5, 56.1, 82.7, 114.6, 122.5, 141.3; LRMS (APCI+): calcd C8H111N3 [M+H]+ 276.1. found 276.0.

Workup

temperatureThe reaction was heated for additional 30 min
concentrationconcentrated in vacuo
customPurification by silica gel column chromatography (1/9 EtOAc/hexanes-7/3 EtOAc/hexanes, gradient)

Sources & evidence

ORD record: ord-7f380bd477674e3ca4b9da5ff2c4b2f7
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034336B2

Reaction notes

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