Cesium carbonate → HCID 21106507, compound

HRID 1783694Notes

Reaction equation

HRID 1783694 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH2:23][CH3:24])[C:20](=[O:22])[CH3:21])=[CH:15][CH:14]=2)[N:3]=1.C(OC([N:32]1[C:36]([CH3:37])=[CH:35][C:34]([NH2:38])=[N:33]1)=O)(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+].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>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].O>[CH2:23]([N:19]([C:16]1[CH:17]=[CH:18][C:13]([N:4]2[N:3]=[C:2]([NH:38][C:34]3[CH:35]=[C:36]([CH3:37])[NH:32][N:33]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]2=[O:12])=[CH:14][CH:15]=1)[C:20](=[O:22])[CH3:21])[CH3:24]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 113215371H-Pyrazole-1-carboxylicacid,3-amino-5-methyl-,1,1-dimethylethylesterHCID 21106603HCID 21106603, compound

Product 1

HCID 21106507HCID 21106507, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Procedure

N-[4-(4-Bromo-1-oxo-1H-phthalazin-2-yl)-phenyl]-N-ethyl-acetamide (0.10 g, 0.027 mmol), 3-amino-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester (0.006 g, 0.03 mmol), Cs2CO3 (0.01 g, 0.03 mmol), tris-(dibenzylideneacetone)-dipalladium (0.001 g, 0.001 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.002 g, 0.003 mmol) under nitrogen were heated to 100° C. for 18 hours, and then allowed to cool to RT. H2O was added and the solvent was evaporated in vacuum. Purification via chromatography gave the title compound (0.003 g, 23% yield). 1H-NMR: (400 MHz, D6-DMSO) 9.28 (1H, s), 8.51 (1H, d), 8.38 (1H, d), 7.99 (1H, t), 7.91 (1H, t), 7.87 (2H, d), 7.41 (2H, d), 6.25 (1H, s), 3.69 (2H, q), 2.20 (3H, s), 1.81 (3H, s), 1.07 (3H, t); MS (ESI+)=403.34 (M+H)+.

Workup

  1. customthe solvent was evaporated in vacuum
  2. customPurification via chromatography

Sources & evidence

ORD record
ord-893af672312646d793f180c0be289a75
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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