1,4-Dioxane → Tert-butyl 4-(5-chloro-6-methoxypyridin-3-yl)-3-methylbenzoate

HRID 529716노트

반응식

HRID 529716 반응식
Br[C:2]1[CH:3]=[C:4]([Cl:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:19][C:20]1[CH:21]=[C:22]([CH:30]=[CH:31][C:32]=1B1OC(C)(C)C(C)(C)O1)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].O1CCOCC1>C(OCC)(=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].ClCCl.[Pd+2].O>[Cl:10][C:4]1[CH:3]=[C:2]([C:32]2[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])=[CH:21][C:20]=2[CH3:19])[CH:7]=[N:6][C:5]=1[O:8][CH3:9]

참가 물질

9

반응물 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 404270045-Bromo-3-chloro-2-methoxypyridineHCID 68937270Tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

생성물 1

HCID 86682280Tert-butyl 4-(5-chloro-6-methoxypyridin-3-yl)-3-methylbenzoate수율 88.8%

시약·촉매·용매 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 17952575palladium(II)dichloromethane촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a 250 mL RBF was added 5-bromo-3-chloro-2-methoxypyridine (1.5 g), tribasic potassium phosphate (2.86 g, 13.5 mmol), bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.275 g, 6.74 mmol), tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (2.27 g, 7.13 mmol), dioxane (50 mL) and water (3 mL). The flask was sealed and was stirred at 80° C. overnight. The reaction was cooled to room temperature, diluted with ethyl acetate, washed with water, filtered and concentrated. The resultant residue was purified by column chromatography to yield tert-butyl 4-(5-chloro-6-methoxypyridin-3-yl)-3-methylbenzoate (2.0 g, 5.99 mmol). MS ESI calc'd. for C18H21ClNO3 [M+H]+ 334.1, found 334.0.

후처리

  1. customThe flask was sealed
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with water
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-15506110a8904d8d95aeca17b1be198c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346825B2

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