Dichloromethane → 2-{[6-(3-Pentanoyl-1-benzofuran-2-yl)-1-phenyl-2-naphthyl]oxy}acetonitrile

HRID 1359218Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=4[C:16]=3[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:27][CH2:28][C:29]#[N:30].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.ClCCl.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[C:17]([C:16]1[C:15]2[CH:23]=[CH:24][CH:25]=[CH:26][C:14]=2[O:13][C:12]=1[C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[C:3]([O:27][CH2:28][C:29]#[N:30])[CH:4]=[CH:5]2)(=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

Conditions

Temperature: 70 °C

Procedure

Following the procedure described in Step 1 of Example 1, 2-{[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile (0.480 g, 1.04 mmol) was coupled to phenylboronic acid (0.448 g, 3.67 mmol) using [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium (II) complex with dichloromethane (1:1) (0.0918 g, 0.112 mmol) in presence of potassium carbonate (0.290 g, 2.10 mmol) in dioxane (10 mL) and water (1.0 mL). The reaction mixture was stirred at 70° C. for 22 hours. Purification by flash chromatography (Biotage apparatus) using 7.5-10% tert-butyl methyl ether in hexane furnished the title compound (0.230 g). 1HNMR (300 MHz, DMSO-d6): δ8.5 (s, 1H), 8.3 (d, 1H, J=9.2 Hz), 8.05 (d, 1H, J=7.7 Hz), 7.7-7.85 (m, 3H), 7.35-7.6 (m, 9H), 5.25 (s, 2H), 2.75 (t, 2H, J=7.7 Hz), 1.5-1.6 (m, 2H), 1.1-1.3 (m, 2H), and 0.75 ppm (t, 3H, J=7.7 Hz).

Workup

customPurification by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record: ord-c7f5d12bda8443d98d68f0d42be47a57
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599925B2

Reaction notes

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