Sodium Carbonate → HCID 69392516, compound

HRID 916848Notes

Reaction equation

[CH3:1][C:2]1([CH3:38])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][O:29][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[C:33](I)[CH:32]=5)=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.[CH3:39][O:40][C:41]([C:43]1[CH:44]=[C:45](B(O)O)[CH:46]=[CH:47][CH:48]=1)=[O:42].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][C:2]1([CH3:38])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][O:29][CH2:30][C:31]5[CH:32]=[C:33]([C:47]6[CH:46]=[CH:45][CH:44]=[C:43]([C:41]([O:40][CH3:39])=[O:42])[CH:48]=6)[CH:34]=[CH:35][CH:36]=5)=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-[2-(4-{2-[(3-iodobenzyl)oxy]ethoxy}phenyl)ethyl]-1,3-oxazolidin-2-one {Example 6 i)} (150 mg), 3-(methoxycarbonyl)phenylboronic acid (47 mg), tetrakis(triphenylphosphine)palladium (0) (6 mg) and 2N sodium carbonate (7 mL) in dimethoxyethane (10 mL) was heated at 85° C. for 1 h. The solution was then diluted in EtOAc, washed with water, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (Biotage, 40 g) eluting with CH2Cl2-MeOH (200:1) to give the title compound (128 mg). LCMS RT=3.99 min.

Workup

washwashed with water
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by chromatography (Biotage, 40 g)
washeluting with CH2Cl2-MeOH (200:1)

Sources & evidence

ORD record: ord-faa48e9692b2446cac51e1d240e998b9
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271197B2

Reaction notes

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