1,2-Dimethoxyethane → HCID 86700859, compound

HRID 881754Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C:15]34[CH2:22][CH2:21][C:18]([CH2:23][C:24]([O:26][CH3:27])=[O:25])([CH2:19][CH2:20]3)[CH2:17][O:16]4)=[CH:11][CH:10]=2)O1.Br[C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37]2[O:38][C:39]([CH:42]3[CH2:45][CH2:44][CH2:43]3)=[N:40][N:41]=2)=[CH:32][CH:31]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(COC)OC>O.CO>[CH:42]1([C:39]2[O:38][C:37]([NH:36][C:33]3[CH:34]=[CH:35][C:30]([C:9]4[CH:14]=[CH:13][C:12]([C:15]56[CH2:20][CH2:19][C:18]([CH2:23][C:24]([O:26][CH3:27])=[O:25])([CH2:21][CH2:22]5)[CH2:17][O:16]6)=[CH:11][CH:10]=4)=[CH:31][CH:32]=3)=[N:41][N:40]=2)[CH2:43][CH2:44][CH2:45]1

Participants

Conditions

Temperature: 80 °C

Procedure

A vial was charged with methyl 2-(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetate (20 mg, 0.052 mmol), N-(4-bromophenyl)-5-cyclobutyl-1,3,4-oxadiazol-2-amine (30.5 mg, 0.104 mmol), PdCl2(dppf)-CH2Cl2adduct (6.34 mg, 7.77 μmol), potassium phosphate (21.98 mg, 0.104 mmol), dimethoxyethane (0.6 ml), methanol (0.2 ml), and water (0.1 ml) at room temperature. The vial was sealed, flushed with nitrogen for three times and heated at 80° C. for 16 hours. The mixture was purified by flash chromatography (heptanes/acetone 1/1, washed with acetone/ethanol 1/1) to afford methyl 2-(1-(4′-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)-[1,1′-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-4-yl)acetate (40 mg, 40% purity, 65% yield) as white solid. LC/MS, ESI-MS(+1) m/z 474.19, RT 1.41 (Condition E).

Workup

customThe vial was sealed
customflushed with nitrogen for three times
customThe mixture was purified by flash chromatography (heptanes/acetone 1/1, washed with acetone/ethanol 1/1)

Sources & evidence

ORD record: ord-34059346a9c6426db58ca7cabaacdbf2
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993619B2

Reaction notes

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