Isopropyl 2-(3-aminophenoxy)acetate → isopropyl 2-(3-((7-(3-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-ylidene)amino)phenoxy)acetate

HRID 1051110Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][CH2:14][C:15]3=O)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][CH:33]=1)[O:23][CH2:24][C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][CH2:14][C:15]3=[N:19][C:20]3[CH:21]=[C:22]([CH:31]=[CH:32][CH:33]=3)[O:23][CH2:24][C:25]([O:27][CH:28]([CH3:29])[CH3:30])=[O:26])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Approximately forty oven dried 3 Å molecular sieves were added to a solution of 7-(3-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-one (174 mg, 0.724 mmol) and isopropyl 2-(3-aminophenoxyl)acetate (644 mg, 3.08 mmol) in toluene (15 mL) at 25° C. The reaction was heated in an 120° C. oil bath and allowed to stir overnight for approximately 16 hours. The reaction was cooled to room temperature and concentrated. The resulting crude residue was purified by combiflash (4 g column, hexanes→100% ethyl acetate/hexanes, gradient) to afford 25 mg (4%) of isopropyl 2-(3-((7-(3-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-ylidene)amino)phenoxy)acetate.

Workup

customApproximately forty oven dried 3 Å molecular sieves
temperatureThe reaction was cooled to room temperature
concentrationconcentrated
customThe resulting crude residue was purified by combiflash (4 g column, hexanes→100% ethyl acetate/hexanes, gradient)

Sources & evidence

ORD record: ord-ab839d683ae9499abe5e6a5f51e6d2d1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388153B2

Reaction notes

Loading…