Triethylamine → 2-{5-[5-(4-Morpholinylcarbonyl)-2-pyridinyl]-1-benzofuran-2-yl}ethanol

HRID 1064692Notes

Reaction equation

I[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[O:15])=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[OH:22].C(N(CC)CC)C.[CH2:30]([OH:34])[CH2:31][C:32]#[CH:33]>CN(C)C=O.ClCCl.O>[N:16]1([C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:6]3[CH:5]=[CH:4][C:3]4[O:22][C:32]([CH2:31][CH2:30][OH:34])=[CH:33][C:2]=4[CH:7]=3)=[N:9][CH:10]=2)=[O:15])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of Example 44C (2.85 g, 6.95 mmol), triethylamine (2.4 mL, 17.4 mmol), and 3-butyn-1-ol (0.73 g, 10.4 mmol) in dimethylformamide (15 mL) at 20° C. was added cuprous iodide (0.2 g, 1.0 mmol) and bis-triphenylphosphine palladium dichloride (0.24 g, 0.35 mmol). The mixture was stirred for one hour, then heated to 65° C. for 16 hours. The reaction was cooled to 23° C., diluted with dichloromethane (200 mL) and water (100 mL). The mixture was stirred with Celite then filtered. The filtrate was washed with water (1×50 mL), the organic phase separated, dried (Na2SO4), filtered and concentrated under reduced pressure to give a tan foam. The residue was chromatographed on silica using 5% methanol in dichloromethane to give the titled compound as a yellow solid (1.83 g, 75%/). MS (DCI) m/z 353 (M+H)+;

Workup

temperatureThe reaction was cooled to 23° C.
stirringThe mixture was stirred with Celite
filtrationthen filtered
washThe filtrate was washed with water (1×50 mL)
customthe organic phase separated
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give a tan foam
customThe residue was chromatographed on silica using 5% methanol in dichloromethane

Sources & evidence

ORD record: ord-e6d9ad59e6114598b68bd61efe448465
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969730B2

Reaction notes

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