Water → HCID 90408790, compound

HRID 1855079Notes

Reaction equation

[C:1]([O:5][C:6](=[O:28])[CH2:7][O:8][CH2:9][CH2:10][C:11]12[CH2:18][CH2:17][C:14]([C:19]3[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=3)([CH2:15][CH2:16]1)[O:13][CH2:12]2)([CH3:4])([CH3:3])[CH3:2].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:29]([C:21]1[CH:20]=[C:19]([C:14]23[CH2:17][CH2:18][C:11]([CH2:10][CH2:9][O:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:28])([CH2:16][CH2:15]2)[CH2:12][O:13]3)[CH:24]=[CH:23][CH:22]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (3-(4-(2-(2-(tert-butoxy)-2-oxoethoxy)ethyl)-2-oxabicyclo[2.2.2]octan-1-yl)phenyl)boronic acid (49A; 20 mg, 0.051 mmol), benzyl bromide (0.012 mL, 0.102 mmol), and Na2CO3 (16 mg, 0.15 mmol) in 1,4-dioxane (1 mL)/water (0.2 mL) was degassed under Ar for 3 min using an ultrasonicator and then (Ph3P)4Pd (59 mg, 0.051 mmol) was added. The reaction was stirred at 100° C. under Ar for 18 h, then was cooled to rt and partitioned between EtOAc (5 mL) and water, dried (MgSO4), and concentrated in vacuo to give the crude product as a yellow oil, which was used in the next reaction without further purification.

Workup

customwas degassed under Ar for 3 min
temperaturewas cooled to rt
custompartitioned between EtOAc (5 mL) and water
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-482928c758c9475686cfe04605850a32
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962660B2

Reaction notes

Loading…