Potassium Carbonate → HCID 118113375, compound

HRID 1485130Notes

Reaction equation

[OH:1][C:2]1[CH2:7][CH2:6][N:5]2[CH:8]([C:11]3[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=3)[CH2:9][O:10][CH:4]2[C:3]=1[C:18]([NH:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[O:19].[F:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1.CO>[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:14]2[CH:15]=[CH:16][C:11]([CH:8]3[N:5]4[CH2:6][CH2:7][C:2]([OH:1])=[C:3]([C:18]([NH:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[O:19])[CH:4]4[O:10][CH2:9]3)=[CH:12][CH:13]=2)=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of the compound (100 mg) obtained in step (3) above, 4-fluorophenylboronic acid (66 mg), palladium(II) acetate (6.6 mg), tri(2-methylphenyl)phosphine (26 mg), potassium carbonate (186 mg), methanol (4.4 mL) and toluene (2.2 mL) was stirred in a sealed tube at 90° C. for 70 minutes. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=99:1-0:100, then chloroform:methanol=100:0-85:15) to give methyl N-{[3-(4′-fluoro-4-biphenylyl)-7-hydroxy-2,3,6,8a-tetrahydro-5H-[1,3]oxazolo[3,2-a]pyridin-8-yl]carbonyl}-glycinate as a pale brown solid (100 mg).

Workup

temperatureAfter being cooled to room temperature
concentrationthe reaction mixture was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (n-hexane

Sources & evidence

ORD record: ord-7fdeaae3dcfa4aa29795675fd862d254
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422240B2

Reaction notes

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