Propargyl alcohol → HCID 10310436, compound

HRID 1268982Notes

Reaction equation

[O:1]=[S:2]1(=[O:28])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[C:23](Br)[N:22]=[N:21]4)[O:16][C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:4][CH2:3]1.[CH2:29]([OH:32])[C:30]#[CH:31]>CN1CCCC1=O.C(N(CC)CC)C.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].[Cu](I)I>[O:1]=[S:2]1(=[O:28])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[C:23]([C:31]#[C:30][CH2:29][OH:32])[N:22]=[N:21]4)[O:16][C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[4-bromo-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (Example 36) (235 mg, 0.5 mmol), propargyl alcohol (42 mg, 0.75 mmol), tetrakis(triphenylphosphine)palladium (0) (29 mg, 5 mol %) and copper iodide (5 mg, 5 mol %) were mixed in N-methylpyrrolidone/triethylamine (5 ml, 5:1). The reaction mixture was flushed with nitrogen and heated to 90° C. for 48 hours. The reaction mixture was filtered and extracted with ethyl acetate/water, the organic phase was concentrated and purified by flash chromatography on silica gel with 5% of methanol in dichloromethane to give the title product (27 mg).

Workup

customThe reaction mixture was flushed with nitrogen
filtrationThe reaction mixture was filtered
extractionextracted with ethyl acetate/water
concentrationthe organic phase was concentrated
custompurified by flash chromatography on silica gel with 5% of methanol in dichloromethane

Sources & evidence

ORD record: ord-24011d7cd8a94ba9b77c05b95b015788
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199143B2

Reaction notes

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