Sodium Carbonate → 4-[2-(2-Hydroxyethyl)-1-benzofuran-4-yl]benzonitrile

HRID 494843Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].[C:12]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)C=CC=[CH:14][C:13]=1P(C1CCCCC1)C1CCCCC1.[C:37]([O-:40])([O-])=O.[Na+].[Na+].C1C=CC=CC=1.C([OH:51])C>C(Cl)Cl.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[OH:51][CH2:14][CH2:13][C:12]1[O:40][C:37]2[CH:36]=[CH:35][CH:34]=[C:33]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[C:32]=2[CH:31]=1

Participants

Conditions

Temperature: 75 °C

Procedure

The product from Example 85C (0.1 g, 0.32 mmol) in 8 mL of benzene/ethanol (2:1), was treated with 4-cyanophenylboronic acid (0.052 g, 0.35 mmol), palladium diacetate (0.0032 mmol), bipheny-2-yl-dicyclohexylphosphine (0.0048 mmol) and Na2CO3 (2M, 0.87 mmol) and heated at 75° C. for 14 hours. The mixture was diluted with 100 mL of CH2Cl2 and washed successively with water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure. The residue was purified by chromatography over silica using CH2Cl2 to provide the title compound (55% yield). 1HNMR (300 MHz, CDCl3) δ 3.10 (m, 2H), 4.05 (m, 2H), 6.62 (s, 1H), 6.90 (m, 1H), 7.25 (m, 2H), 7.52 (m, 2H), 7.73 (m, 2H). MS (CDI) m/z 264 (M+H)+.

Workup

washwashed successively with water (100 mL) and brine (100 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
customthe filtrate was evaporated under reduced pressure
customThe residue was purified by chromatography over silica

Sources & evidence

ORD record: ord-e6ec0945364e4659abbc8ad963d14ca3
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538138B2

Reaction notes

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