1,2-Dimethoxyethane → HCID 86700863, compound

HRID 881756Notes

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]([C:39]2[O:43][C:42]([CH2:44][CH3:45])=[N:41][C:40]=2[CH3:46])=[O:38])=[CH:32][CH:31]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(COC)OC>O.C(O)C>[CH2:44]([C:42]1[O:43][C:39]([C:37]([NH:36][C:33]2[CH:34]=[CH:35][C:30]([C:9]3[CH:10]=[CH:11][C:12]([C:15]45[CH2:22][CH2:21][C:18]([CH2:23][C:24]([O:26][CH3:27])=[O:25])([CH2:19][CH2:20]4)[CH2:17][O:16]5)=[CH:13][CH:14]=3)=[CH:31][CH:32]=2)=[O:38])=[C:40]([CH3:46])[N:41]=1)[CH3:45]

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 (14 mg, 0.036 mmol), N-(4-bromophenyl)-2-ethyl-4-methyloxazole-5-carboxamide (22.4 mg, 0.072 mmol), PdCl2(dppf)-CH2Cl2adduct (4.44 mg, 5.44 μmol), potassium phosphate (15.4 mg, 0.072 mmol), dimethoxyethane (0.6 ml), ethanol (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′-(2-ethyl-4-methyloxazole-5-carboxamido)-[1,1′-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-4-yl)acetate (25 mg, 40% purity, 56% yield) as white solid. LC/MS, ESI-MS(+1) m/z 489.1, RT 1.53 (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-0cebea04d7094bb3bb2e3e4695dedccd
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993619B2

Reaction notes

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