1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 67343427, compound

HRID 451485Notes

Reaction equation

HRID 451485 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)[CH:3]=1.Br[C:16]1[N:40]=[C:19]2[C:20]([C:25]3[CH:26]=[C:27]([CH:37]=[CH:38][CH:39]=3)[CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:21][C:22]([CH3:24])=[CH:23][N:18]2[N:17]=1.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.[O-]C1C=CC=CC=1.[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.C(Cl)(Cl)Cl.[Pd].[Pd].C(Cl)Cl>[CH3:24][C:22]1[CH:21]=[C:20]([C:25]2[CH:26]=[C:27]([CH:37]=[CH:38][CH:39]=2)[CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:33])[CH3:34])[C:19]2[N:18]([N:17]=[C:16]([NH:14][CH:11]3[CH2:12][CH2:13][N:8]([C:4]4[CH:3]=[C:2]([CH3:1])[N:7]=[CH:6][N:5]=4)[CH2:9][CH2:10]3)[N:40]=2)[CH:23]=1

Participants

8

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 4445035Phenolate SodiumHCID 166433141-(6-Methylpyrimidin-4-yl)piperidin-4-amineHCID 67342864Tert-butyl 3-(2-bromo-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-8-yl)benzylcarbamate

Product 1

HCID 67343427HCID 67343427, compound

Reagents, catalysts & solvents 3

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(6-methylpyrimidin-4-yl)piperidin-4-amine (52.5 mg, 273 μmol), tert-butyl 3-(2-bromo-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-8-yl)benzylcarbamate (114 mg, 273 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (12.6 mg, 21.9 μmol), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (11.3 mg, 10.9 μmol) and sodium phenoxide (50.1 mg, 410 μmol) in dioxane (3 mL) was degassed three times and reacted at 140° C. under an atmosphere of nitrogen in a microwave oven for 1 hour. The title compound was obtained a light yellow solid (46 mg, 32%) after column chromatography on silica gel using a gradient from methylenechloride to a mixture of methylenechlorid/methanol 19:1 (v/v) as eluent.

Workup

  1. customreacted at 140° C. under an atmosphere of nitrogen in a microwave oven for 1 hour

Sources & evidence

ORD record
ord-1af8b2159f8742c8ac88f93872e9df17
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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