Potassium Phosphate, Tribasic → 2-tert-butyl-5-(3-(5-(1,5-dimethyl-1H-pyrazol-3-ylamino)-6-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,6-dihydropyridazin-3-yl)-2-methylphenyl)-4H-pyrrolo[3,4-d]thiazol-6(5H)-one

HRID 872181Notes

Reaction equation

HRID 872181 reaction equation
[C:1]([C:5]1[S:6][C:7]2[C:12](=[O:13])[N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16](B4OC(C)(C)C(C)(C)O4)[C:15]=3[CH3:29])[CH2:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:31]1[CH:32]=[C:33]([NH:46][C:47]2[CH:51]=[C:50]([CH3:52])[N:49]([CH3:53])[N:48]=2)[C:34](=[O:45])[N:35]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[N:36]=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.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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].O1CCOCC1>[C:1]([C:5]1[S:6][C:7]2[C:12](=[O:13])[N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:31]4[CH:32]=[C:33]([NH:46][C:47]5[CH:51]=[C:50]([CH3:52])[N:49]([CH3:53])[N:48]=5)[C:34](=[O:45])[N:35]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:42])([CH3:44])[CH3:43])[N:36]=4)[C:15]=3[CH3:29])[CH2:10][C:8]=2[N:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 585403246-chloro-4-(1,5-dimethyl-1H-pyrazol-3-ylamino)-2-((2-(trimethyl-silyl)ethoxy)methyl)pyridazin-3(2H)-oneHCID 666348992-tert-Butyl-5-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4H-pyrrolo[3,4-d]thiazol-6(5H)-one

Product 1

HCID 666135272-tert-butyl-5-(3-(5-(1,5-dimethyl-1H-pyrazol-3-ylamino)-6-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,6-dihydropyridazin-3-yl)-2-methylphenyl)-4H-pyrrolo[3,4-d]thiazol-6(5H)-oneYield 60%

Reagents, catalysts & solvents 3

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

Procedure

Following Example 109, 247.2 mg (0.6 mmol) of 2-tert-butyl-5-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4H-pyrrolo[3,4-d]thiazol-6(5H)-one 109f, 185 mg (0.5 mmol) of 6-chloro-4-(1,5-dimethyl-1H-pyrazol-3-ylamino)-2-((2-(trimethylsilyl)ethoxy)methyl)pyridazin-3(2H)-one 110b, 45.8 mg (0.05 mmol) of tris(dibenzylideneacetone)dipalladium(0), 49.3 mg (0.12 mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.596 mmol), 0.67 mL (0.85 mmol) of 1.27 M of potassium phosphate in water, and 10 mL of 1,4-dioxane were reacted to afford 186 mg (60%) of 2-tert-butyl-5-(3-(5-(1,5-dimethyl-1H-pyrazol-3-ylamino)-6-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,6-dihydropyridazin-3-yl)-2-methylphenyl)-4H-pyrrolo[3,4-d]thiazol-6(5H)-one 110c.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-d8c9e21f9b06495ea7e4c8f0d515222c
Source dataset
uspto-grants-2015_03
Patent number
US08975260B2

Reaction notes

Loading…