Potassium Carbonate → 2-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-4-methyl-oxazole-5-carboxylic acid ethyl ester

HRID 1025574Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([C:16]1[CH:26]=[CH:25][CH:24]=[C:23](B3OC(C)(C)C(C)(C)O3)[C:17]=1[CH2:18][O:19][C:20](=[O:22])[CH3:21])[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[CH2:36]([O:38][C:39]([C:41]1[O:45][C:44](Br)=[N:43][C:42]=1[CH3:47])=[O:40])[CH3:37].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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]>[CH2:36]([O:38][C:39]([C:41]1[O:45][C:44]([C:23]2[CH:24]=[CH:25][CH:26]=[C:16]([N:10]3[N:9]=[CH:8][C:7]4[C:12](=[CH:13][CH:14]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH:6]=4)[C:11]3=[O:15])[C:17]=2[CH2:18][O:19][C:20](=[O:22])[CH3:21])=[N:43][C:42]=1[CH3:47])=[O:40])[CH3:37]

Participants

Conditions

Temperature: 100 °C

Procedure

Under N2, acetic acid 2-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl ester (preparation described in intermediate-4, 72 mg, 0.153 mmol), 2-bromo-4-methyl-oxazole-5-carboxylic acid ethyl ester (34 mg, 0.146 mmol), Pd(dppf)Cl2 (36 mg, 0.0438 mmol) and K2CO3 (61 mg, 0.438 mmol) were dissolved in dioxane/H2O (5:1, 6 mL). The reaction mixture was stirred at 100° C. for about 1.5 h. The solvent was removed under reduced pressure, and the residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=2:1) to give 2-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-4-methyl-oxazole-5-carboxylic acid ethyl ester.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=2:1)

Sources & evidence

ORD record: ord-2f3313be377c49d7b3c10aa8861be017
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729078B2

Reaction notes

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