Water → HCID 57937593, compound

HRID 1435109Notes

Reaction equation

Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH3:12][N:13]1[CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:15]=[N:14]1.C([O-])([O-])=O.[Na+].[Na+].O>CC(N(C)C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[CH3:12][N:13]1[CH:17]=[C:16]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=2)[CH:15]=[N:14]1

Participants

Conditions

Temperature: 80 °C

Procedure

4-Bromo-2-nitroaniline (1.0 g, 4.6 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.1 g, 5.1 mmol) were dissolved in 13 ml of DMA, placed under nitrogen, and heated to 80° C. A 2N aqueous solution of Na2CO3 was added, followed by PdCl2(dppf) dichloromethane adduct (0.076 g, 0.90 mmol). Reaction was stirred at 80° C. for 1 h and then cooled to rt, poured into 150 ml of water and extracted with EtOAc (3×), Combined organics were dried over anhydrous MgSO4, filtered, concentrated onto silica gel, and purified by flash chromatography using 0-50% EtOAc/hexanes. 4-(1-Methyl-1H-pyrazol-4-yl)-2-nitroaniline was isolated as a bright orange solid (1.0 g, 99%). MS (ESI): 219 [M+H]+.

Workup

customReaction
temperaturecooled to rt
extractionextracted with EtOAc (3×)
dry with materialCombined organics were dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated onto silica gel
custompurified by flash chromatography

Sources & evidence

ORD record: ord-574c9333d2a54e2da14ff13b205a6509
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615643B2

Reaction notes

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