3-Iodopyridine → HCID 21094027, compound

HRID 729732Notes

Reaction equation

C1C=CC(P(C2C(OC3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=3)=CC=CC=2)C2C=CC=CC=2)=CC=1.I[C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1.[SH:47][C:48]1[CH:53]=[CH:52][C:51]([CH:54]([CH2:63][CH:64]2[CH2:69][CH2:68][O:67][CH2:66][CH2:65]2)[C:55]([NH:57][C:58]2[S:59][CH:60]=[CH:61][N:62]=2)=[O:56])=[CH:50][CH:49]=1.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.C(Cl)Cl.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]>[N:43]1[CH:44]=[CH:45][CH:46]=[C:41]([S:47][C:48]2[CH:53]=[CH:52][C:51]([CH:54]([CH2:63][CH:64]3[CH2:69][CH2:68][O:67][CH2:66][CH2:65]3)[C:55]([NH:57][C:58]3[S:59][CH:60]=[CH:61][N:62]=3)=[O:56])=[CH:50][CH:49]=2)[CH:42]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A solution of Pd2dba3 (18 mg, 20 μmol) and DPEPhos (24 mg, 45 μmol) in anhydrous PhMe (4 mL) was stirred at 20° C. for 3 min. 3-Iodopyridine (107 mg, 522 μmol), 2-(4-mercaptophenyl)-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylpropionamide (see EXAMPLE 146, 173 mg, 500 μmol), and t-BuOK (65 mg, 579 μmol) were added, then the mixture was heated at 105° C. (bath) for 2.5 h. On cooling to 20° C., the mixture was diluted with CH2Cl2 (10 mL) and filtered through Celite, washing with CH2Cl2 (5 mL) and EtOAc (10 mL). Solvent evaporation and flash chromatography (IH-EtOAc, 3:1 to 0:1) afforded the title compound: RTB=1.37 min; m/z (ES+)=426.0 [M+H]+.

Workup

temperatureOn cooling to 20° C.
filtrationfiltered through Celite
washwashing with CH2Cl2 (5 mL) and EtOAc (10 mL)
customSolvent evaporation and flash chromatography (IH-EtOAc, 3:1 to 0:1)

Sources & evidence

ORD record: ord-5f485e1ee42d48e885ba05eaca3e27c5
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582632B2

Reaction notes

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