Iodine → HCID 90111713, compound

HRID 623715

Reaction equation

[CH2:1]([O:3][C:4]1[C:5]([C:16]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)=O)=[N:6][N:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[N:8]=1)[CH3:2].II.[PH2](O)=O.[OH-].[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH2:1]([O:3][C:4]1[C:5]([CH2:16][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=2)=[N:6][N:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[N:8]=1)[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of [5-ethoxy-2-(4-fluorophenyl)-2H-1,2,3-triazol-4-yl][2-(trifluoromethyl)-4-pyridinyl]methanone (i.e. the product of Step C, 2.7 g, 7.1 mmol) in acetic acid (15 mL) was added iodine (1.8 g, 7.1 mmol) and hypophosphorous acid (50% in water, 3.1 mL, 28.4 mmol). The mixture was heated to 110° C. under a nitrogen atmosphere for 6 h. The reaction mixture was cooled to 23° C. and neutralized to ˜pH 7 with 1 M NaOH and a saturated aqueous sodium bicarbonate solution. The mixture was extracted with ethyl acetate (2×15 mL), dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes to afford the title compound (2.1 g) as an off-white solid.

Workup

temperatureThe reaction mixture was cooled to 23° C.
extractionThe mixture was extracted with ethyl acetate (2×15 mL)
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure
customThe crude residue was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-637180d00d444c1e88d1d15f9f75df97
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302999B2

Linked notes

Loading…