3-(5-Cyclohex-1-enyl-1H-inden-2-ylmethoxy)-2,6-difluoro-benzamide → 3-(5-Cyclohexyl-1H-inden-2-ylmethoxy)-2,6-difluoro-benzamide

HRID 538594Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[CH2:12][C:11]([CH2:16][O:17][C:18]2[C:19]([F:28])=[C:20]([C:24]([F:27])=[CH:25][CH:26]=2)[C:21]([NH2:23])=[O:22])=[CH:10]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>CO.[Pd]>[CH:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[CH2:12][C:11]([CH2:16][O:17][C:18]2[C:19]([F:28])=[C:20]([C:24]([F:27])=[CH:25][CH:26]=2)[C:21]([NH2:23])=[O:22])=[CH:10]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-(5-Cyclohex-1-enyl-1H-inden-2-ylmethoxy)-2,6-difluoro-benzamide (0.01 g, 0.25 mmol) in 5 ml of anhydrous methanol was added Pd—C (10%, 100 mg). The reaction mixture was stirred at 25° C. for 48 h under hydrogen atmosphere. The reaction mixture was filtered over the bed of celite and evaporated to dryness under reduced pressure to give the title compound as white solid (0.01 g, 10%). 1H NMR (DMSO-d6, 400 MHz); δ 1.40 (m, 6H), 1.72 (m, 4H), 2.63 (m, 1H), 5.66 (s, 2H), 7.09 (m, 1H), 7.35 (m, 2H), 7.83 (br s, 1H), 7.89 (d, J=8.40 Hz, 1H), 7.99 (d, J=8.40 Hz, 1H) and 8.18 (br s, 1H). MS ES+ (403.33), HPLC (method II) Rt=18.76 min.

Workup

filtrationThe reaction mixture was filtered over the bed of celite
customevaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-8f3eacae6ff349c882f47c0bc8b6492b
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865736B2

Reaction notes

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