HCID 22475120, compound → HCID 22475161, compound

HRID 2103128Notes

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]>CN1C(=O)CCC1>[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-methyl pyrrolidinone (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-6a550e13b0a64e2595b276d23f260fbb
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576088B2

Reaction notes

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