Cesium carbonate → HCID 21106507, compound

HRID 1765381Notes

Reaction equation

HRID 1765381 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 room temperature. 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-e312d2acd0a94bdfa899e6e84e488719
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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