Diiodomethane → 1-(2-fluoro-4-hydroxyphenyl)-5-iodo-3-methyl-1H-pyrazole-4-carbonitrile

HRID 1410167Notes

Reaction equation

N[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=2[F:14])[N:5]=[C:4]([CH3:15])[C:3]=1[C:16]#[N:17].[I:18]CI.N(OCCC(C)C)=O>CC#N.C(Cl)Cl>[F:14][C:8]1[CH:9]=[C:10]([OH:13])[CH:11]=[CH:12][C:7]=1[N:6]1[C:2]([I:18])=[C:3]([C:16]#[N:17])[C:4]([CH3:15])=[N:5]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 5-amino-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (114 mg, 0.49 mmol) in MeCN (2.5 mL) was added diiodomethane (0.293 mL, 3.63 mmol) followed by isoamyl nitrite (0.029 mL, 0.216 mmol). The reaction vessel was heated using a heating gun to initiate the reaction. After the rest of isoamyl nitrite (0.261 mL, 1.94 mmol) was added and the reaction was stirred for 1 hour at 50° C. The reaction was diluted with DCM and concentrated into silica and purified using silica gel (Heptane-EtOAc 1:0 to 0:1) to give 1-(2-fluoro-4-hydroxyphenyl)-5-iodo-3-methyl-1H-pyrazole-4-carbonitrile (90.0 mg, 53%).

Workup

temperatureThe reaction vessel was heated
customthe reaction
concentrationconcentrated into silica
custompurified

Sources & evidence

ORD record: ord-f5cbdcb3ba87493a9d03ffa2f976f224
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921402B2

Reaction notes

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