Potassium Carbonate → HCID 10320864, compound

HRID 1782091Notes

Reaction equation

[N+]1([O-:7])C=CC=CC=1.[F:8][C:9]1[CH:10]=[C:11]([N:27]2[CH2:31][C@H:30]([CH2:32][N:33]3[CH:37]=[CH:36][N:35]=[N:34]3)[O:29][C:28]2=[O:38])[CH:12]=[CH:13][C:14]=1[C:15]1[CH:16]=[N:17][C:18]([C:21]2[N:22]=[N:23][N:24]([CH3:26])[N:25]=2)=[CH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O.C1(P([Pd-4](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)C=CC=CC=1>[F:8][C:9]1[CH:10]=[C:11]([N:27]2[CH2:31][C@H:30]([CH2:32][N:33]3[CH:37]=[CH:36][N:35]=[N:34]3)[O:29][C:28]2=[O:38])[CH:12]=[CH:13][C:14]=1[C:15]1[CH:16]=[N+:17]([O-:7])[C:18]([C:21]2[N:22]=[N:23][N:24]([CH3:26])[N:25]=2)=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 75 °C

Procedure

The above sample of pyridine oxide was combined with (5R)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (335 mg, 0.86 mMol, prepared as in Example 1), potassium carbonate (400 mg, 2.9 mMol), and tetrakis(triphenylphosphino)palladium(0) (80 mg, 0.07 mMol) and suspended in THF (10 ml) and water (1 ml). The mixture was heated at 75° C. for 2 hours, then diluted with water. The precipitated solids were collected on a filter, rinsed with water, ether and 1:1 methylene chloride:hexane and dried in vacuo to give the pure product as an off-white solid, 134 mg.

Workup

customThe precipitated solids were collected on a filter
washrinsed with water, ether and 1:1 methylene chloride
dry with materialhexane and dried in vacuo

Sources & evidence

ORD record: ord-3f12a9403865430ba3903a2d8356e26d
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07498350B2

Reaction notes

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