3-(Trifluoromethoxy)aniline → HCID 67338962, compound

HRID 2092300Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[C:7]([I:13])[C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:14])[N:3]=1.[F:15][C:16]([F:26])([F:25])[O:17][C:18]1[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=1>CC(O)C>[I:13][C:7]1[C:8]([CH3:12])=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([CH3:14])[N:3]=[C:2]2[NH:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([O:17][C:16]([F:15])([F:25])[F:26])[CH:19]=1

Participants

Conditions

Temperature: 170 °C

Procedure

4-Chloro-8-iodo-2,7-dimethylquinazoline (0.30 g, 0.94 mmol) and 3-(trifluoromethoxy)benzenamine (0.20 g, 1.1 mmol) were placed in a microwave vial containing 3 mL of IPA. The vial was capped and heated in a microwave reactor at 170° C. for 10 min. The mixture was concentrated in vacuo and the residue was taken up in ethyl acetate and washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was dried with sodium sulfate, concentrated and purified by column chromatography on silica gel using a gradient of 20 to 60% EtOAc in hexanes to give a 8-iodo-2,7-dimethyl-N-(3-(trifluoromethoxy)phenyl)quinazolin-4-amine (0.32 g, 74%) as an off-white solid. MS (M+H)+ 460.

Workup

customThe vial was capped
concentrationThe mixture was concentrated in vacuo
washwashed (2×) with an aqueous saturated solution of sodium bicarbonate
dry with materialThe organic layer was dried with sodium sulfate
concentrationconcentrated
custompurified by column chromatography on silica gel using a gradient of 20 to 60% EtOAc in hexanes

Sources & evidence

ORD record: ord-35edadf261a14e75963cee1bad42e992
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440674B2

Reaction notes

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