Cyclopropyl methyl ketone → HCID 10236997, compound

HRID 335595Notes

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-ed00db5d14744a999394d337a2bc4d7c
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884017B2

Reaction notes

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