Aniline → Methyl 3-anilino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

HRID 501

반응식

HRID 501 반응식
COC(=O)c1cc(Cl)cc(B2OC(C)(C)C(C)(C)O2)c1.Nc1ccccc1>CC(C)(C)P(C(C)(C)C)C(C)(C)C.COCCOC.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=P([O-])([O-])[O-].[K+].[K+].[K+].[Pd].[Pd]>COC(=O)c1cc(Nc2ccccc2)cc(B2OC(C)(C)C(C)(C)O2)c1

참가 물질

7

반응 조건

온도
100 °C

실험 절차

aniline (0.162 mL, 1.78 mmol) was added to methyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (440mg, 1.48 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (13.59 mg, 0.01 mmol), tri- tert-butylphosphine (10.80 µL, 0.04 mmol) and potassium phosphate (441 mg, 2.08 mmol) in degassed DME (6 mL) at 20°C under nitrogen. The reaction was stirred at 100 °C for 2 days. The reaction mixture was diluted with Et2O (50 mL), and washed sequentially with water (50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated. The crude product was purified by flash silica chromatography, elution 10 to 60% EtOAc in heptane.

출처 및 근거

ORD 기록
ord-fbf696d6dcb34e7c9c731cbe586b831a
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
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