HCID 22475120, compound → HCID 22475161, compound

HRID 2184132Notes

Reaction equation

Br[C:2]1[C:3]([C:23]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:24])=[CH:4][C:5]2[O:9][C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:7][C:6]=2[CH:22]=1.[Cu](C#N)[C:32]#[N:33]>CN1CCCC1=O>[N:25]1([C:23]([C:3]2[C:2]([C:32]#[N:33])=[CH:22][C:6]3[O:7][C:8]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[O:9][C:5]=3[CH:4]=2)=[O:24])[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of (6-bromo-2,2-diphenyl-benzo[1,3]dioxol-5-yl)-morpholin-4-yl-methanone, (204 mg, 0.437 mmol) and copper cyanide (102 mg, 1.139 mmol, 2.6 eq.) in N-methylpyrrolidinone (3 mL) was heated at 190° C. during 16 h. The reaction mixture partitioned between water and ethyl acetate. The organic layer was washed with brine and evaporated in vacuo. Purification by flash chromatography afforded the title compound (4.656 g, 83%) as an off white solid.

Workup

customThe reaction mixture partitioned between water and ethyl acetate
washThe organic layer was washed with brine
customevaporated in vacuo
customPurification by flash chromatography

Sources & evidence

ORD record: ord-0917c779d052402daebb455fbc205d68
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900227B2

Reaction notes

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