1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 5-(4-(2-(t-Butyldimethylsilyloxy)ethyl)piperidin-1-yl)-2-chloropyridine

HRID 79180

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[Si:9]([O:16][CH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>O1CCOCC1.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]>[Si:9]([O:16][CH2:17][CH2:18][CH:19]1[CH2:20][CH2:21][N:22]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[N:3][CH:4]=2)[CH2:23][CH2:24]1)([C:12]([CH3:14])([CH3:15])[CH3:13])([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

2-chloro-5-iodopyridine (1.00 g, 4.18 mmol), compound 292 (1.02 g, 4.18 mmol), Tris(dibenzylideneacetone)dipalladium (0) (0.191 g, 0.209 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.242 g, 0.418 mmol), and sodium t-butoxide (0.803 g, 8.35 mmol) were dissolved in 20 mL dioxane. The reaction was purged with argon and heated at 80° C. for 16 hours. The solvent was removed in vacuo and silica gel chromatography (gradient elution hexanes/0-10% ethyl acetate) afforded compound 293 as a beige solid (597 mg, 40%).

Workup

customThe reaction was purged with argon
customThe solvent was removed in vacuo and silica gel chromatography (gradient elution hexanes/0-10% ethyl acetate)

Sources & evidence

ORD record: ord-894b6f7d240e44efa386e0555428b34d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841312B2

Linked notes

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