Triethylamine → HCID 44546737, compound

HRID 1967425Notes

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:23][NH:24][CH3:25])[CH:20]=[CH:21][CH:22]=1.C(N(CC)CC)C>ClCCl>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=1)[CH2:23][N:24]([CH3:25])[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of α-bromo-2′-acetonaphthone (386.2 g, 1.57 mol) in dichloromethane (2.5 L) at 0° C. was added Compound 3 (249.1 g, 1.65 mol) in 30 min, followed by the addition of triethylamine (220.7 mL, 1.57 mmol) in 45 min. After stirring at 0° C. for 40 min, the reaction mixture was warmed to room temperature and stirred overnight. The reaction solution was then washed with water (2×) and the aqueous layer was re-extracted with dichloromethane (2×). The combined organic extract was dried over sodium sulfate and concentrated in vacuo. The ketone, Compound 4, was obtained as a reddish oil (513.3 g, quantitative), was used in the next step without further purification: 1H NMR (CDCl3, 500 MHz) δ 8.50 (s, 1H), 8.01 (d, J=8.5 Hz, 1H), 7.92 (d, 8.0 Hz, 1H), 7.88-7.85 (m, 2H), 7.60-7.54 (m, 2H), 7.26-7.23 (m, 1H), 6.97-6.94 (m, 2H), 6.82 (dd, J=8.0, 2.5 Hz, 1H), 3.88 (s, 2H), 3.75 (s, 3H), 3.69 (s, 2H), 2.42 (s, 3H); ESI MS m/z 320 [M+H]+.

Workup

temperaturethe reaction mixture was warmed to room temperature
stirringstirred overnight
washThe reaction solution was then washed with water (2×)
extractionthe aqueous layer was re-extracted with dichloromethane (2×)
extractionThe combined organic extract
dry with materialwas dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a45902cc3f00498b889dd8955caf41e3
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420811B2

Reaction notes

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