Methyl 2-amino-5-iodo-4-(trifluoromethyl)benzoate → HCID 59164500, compound

HRID 1894049Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](I)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[NH2:15].[CH3:17][C:18]1[CH:22]=[C:21]([Sn](CCCC)(CCCC)CCCC)[N:20]([CH2:36][CH2:37][O:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[N:19]=1>O1CCOCC1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:21]2[N:20]([CH2:36][CH2:37][O:38][CH2:39][Si:40]([CH3:41])([CH3:43])[CH3:42])[N:19]=[C:18]([CH3:17])[CH:22]=2)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[NH2:15]

Participants

Conditions

Temperature: 90 °C

Procedure

2-Amino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (583 mg, 1.69 mmol) and 3-methyl-5-tributylstannanyl-1-(2-trimethylsilanylmethoxy-ethyl)-1H-pyrazole (847 mg, 1 equiv) were weighed in air and added to a flame-dried flask. Bistriphenylphosphinedichloropalladium (119 mg, 0.1 equiv) was added. Dioxane (15 mL) was added and the mixture was stirred for 18 h at 90° C. The mixture was evaporated to dryness. The crude product was purified by flash chromatography (hexanes to EtOAc/hexanes (1:4)) to furnish 2-amino-5-[5-methyl-2-(2-trimethylsilanylmethoxy-ethyl)-2H-pyrazol-3-yl]-4-trifluoromethyl-benzoic acid methyl ester (426 mg, 59%) as a yellow paste (ESI-MS: m/z 430.5 [M+H]+, rt 6.54 min).

Workup

additionadded to a flame-dried flask
additionBistriphenylphosphinedichloropalladium (119 mg, 0.1 equiv) was added
customThe mixture was evaporated to dryness
customThe crude product was purified by flash chromatography (hexanes to EtOAc/hexanes (1:4))

Sources & evidence

ORD record: ord-c531c19e32414bed87e5edd62dfd52fb
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513268B2

Reaction notes

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