Potassium Carbonate → HCID 86700054, 화합물

HRID 1428103노트

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HRID 1428103 반응식
[CH3:1][O:2][C:3]1[CH:16]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:14]=[CH:13][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].[Br:32][C:33]1[C:34]([NH2:40])=[N:35][CH:36]=[C:37](I)[CH:38]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:32][C:33]1[C:34]([NH2:40])=[N:35][CH:36]=[C:37]([C:15]2[CH:14]=[CH:13][C:4]([O:5][CH2:6][CH2:7][N:8]3[CH2:9][CH2:10][CH2:11][CH2:12]3)=[C:3]([O:2][CH3:1])[CH:16]=2)[CH:38]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 176094413-Bromo-5-iodopyridin-2-amineHCID 68934529HCID 68934529, 화합물

생성물 1

HCID 86700054HCID 86700054, 화합물수율 61.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

1-{2-[2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl}pyrrolidine (5.81 g), tetrakis(triphenylphosphine)palladium (0.97 g) and potassium carbonate (6.94 g) were added to a solution of 3-bromo-5-iodopyridin-2-amine (5.00 g) in dioxane (40 ml) and water (4 ml) at room temperature. The reaction mixture was stirred at 80° C. overnight. The reaction mixture was returned to room temperature and a saturated aqueous sodium bicarbonate solution was added, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=50:1->20:1->10:1 (v/v)] to give 4.03 g of the title compound as an oily substance.

후처리

  1. customwas returned to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [chloroform:methanol=50:1->20:1->10:1 (v/v)]

출처 및 근거

ORD 기록
ord-3f538baf6e22472cb49e0cb81c7e88bc
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933103B2

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