Potassium Phosphate, Tribasic → HCID 86712848, compound

HRID 1423991Notes

Reaction equation

HRID 1423991 reaction equation
[Si:1]([O:8][CH2:9][C:10]1([CH3:30])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26](Cl)=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.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:1]([O:8][CH2:9][C:10]1([CH3:30])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26]([C:35]5[CH:36]=[CH:37][C:32]([CH3:31])=[CH:33][CH:34]=5)=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 79799Tolylboronic acidHCID 867128348-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-3-[1-(4-chlorophenyl)cyclopropyl]-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

Product 1

HCID 86712848HCID 86712848, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of the compound (324 mg, 0.7 mmol) obtained in Example 1-2), 4-methylphenylboronic acid (105 mg, 0.77 mmol), tris(dibenzylideneacetone)dipalladium(0) (32 mg, 0.04 mmol), tricyclohexylphosphine (24 mg, 0.08 mmol), and tripotassium phosphate (260 mg, 1.2 mmol) in dioxane (2 mL) and water (1 mL) was stirred at 140° C. for 2 h under microwave irradiation. The reaction mixture was purified by silica gel chromatography (Isco Combiflash, 12 g, hexane:ethyl acetate=0:100 to 100:0, gradient) to obtain the title compound (155 mg, 43%) as a brown oily substance.

Workup

  1. customThe reaction mixture was purified by silica gel chromatography (Isco Combiflash, 12 g, hexane:ethyl acetate=0:100 to 100:0, gradient)

Sources & evidence

ORD record
ord-4c7c7f4659db434194b0fabd474d591a
Source dataset
uspto-grants-2015_01
Patent number
US08927536B2

Reaction notes

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