Cyclopropyl methyl ketone → HCID 10236997, compound

HRID 658199Notes

Reaction equation

[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[O:13][C:14]3[CH:20]=[C:19](Br)[CH:18]=[CH:17][C:15]=3[CH:16]=1)=[O:11])[CH2:2]2.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+].[CH:74]1([C:77]([CH3:79])=[O:78])[CH2:76][CH2:75]1>O1CCOCC1>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[O:13][C:14]3[CH:20]=[C:19]([CH2:79][C:77]([CH:74]4[CH2:76][CH2:75]4)=[O:78])[CH:18]=[CH:17][C:15]=3[CH:16]=1)=[O:11])[CH2:2]2

Participants

Conditions

Temperature: 85 °C

Procedure

150 mg (0.43 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromo-1-benzofuran-2-carboxamide, 27 mg (0.04 mmol) of rac-BINAP, 45 mg (0.47 mmol) of sodium tert-butoxide and 20 mg (0.02 mmol) of tris(benzylideneacetone)dipalladium are dried under high vacuum for 1 h. Under an atmosphere of argon, 2 ml of dioxane are added. 72 mg (0.86 mmol) of methyl cyclopropyl ketone are added dropwise, and the mixture is heated at 85° C. overnight. The crude product is purified by preparative HPLC. The solvent is removed under reduced pressure. Finally, any last solvent residues are removed under high vacuum. 75 mg (50% of theory) of the title compound are isolated.

Workup

customThe crude product is purified by preparative HPLC
customThe solvent is removed under reduced pressure
customFinally, any last solvent residues are removed under high vacuum

Sources & evidence

ORD record: ord-09907830d5744373b509b520557a8ab8
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076355B2

Reaction notes

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