Iodine → Ethyl 1-[4-iodo-6-(2-methoxy-5-methylphenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1255205Notes

Reaction equation

N(OC(C)(C)C)=O.N[C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])[N:12]=[C:11]([N:24]2[C:28]([C:29]([F:32])([F:31])[F:30])=[C:27]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:26]=[N:25]2)[CH:10]=1.[I:38]I>C(Cl)(Cl)Cl>[I:38][C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])[N:12]=[C:11]([N:24]2[C:28]([C:29]([F:32])([F:31])[F:30])=[C:27]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:26]=[N:25]2)[CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Tert-butyl nitrite (0.68 mL, 0.59 mmol) was added to a solution of the title compound from Example 19 Step E (1.2 g, 2.9 mmol) and iodine (0.87 g, 3.4 mmol) in chloroform (20 mL). The resulting mixture was heated at 60° C. for 30 min, cooled and quenched with aqueous sodium sulfite. Extraction with hexane-EtOAc, followed by silica gel flash chromatography using Hexane-EtOAc (20/1 to 7/1) provided the title compound: LCMS m/z 532.6 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.54 (d, J=1.1 Hz, 1H), 8.15 (s, 1H), 7.98 (d, J=1.1 Hz, 1H), 7.79 (d, J=2.1 Hz, 1H), 7.25 (dd, J=8.5 Hz, 2.1 Hz, 1H), 6.94 (d, J=8.5 Hz, 1H), 4.43 (q, J=7.1 Hz, 2H), 3.93 (s, 3H), 2.39 (s, 3H), 1.42 (t, J=7.1 Hz, 3H).

Workup

temperaturecooled
customquenched with aqueous sodium sulfite
extractionExtraction with hexane-EtOAc

Sources & evidence

ORD record: ord-64aab6e373af4964ab1c63646a1f1ea1
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455638B2

Reaction notes

Loading…