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Potassium Carbonate → 3-(4-Aminophenyl)-5-{4-[(2R)-1,4-dioxan-2-ylmethoxy]-3-methoxyphenyl}pyridin-2-amine

HRID 1428106
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HRID 1428106 반응식
Br[C:2]1[C:3]([NH2:24])=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@H:16]3[CH2:21][O:20][CH2:19][CH2:18][O:17]3)=[C:10]([O:22][CH3:23])[CH:9]=2)[CH:7]=1.CC1(C)C(C)(C)OB([C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(Cl)(Cl)Cl.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>[NH2:37][C:36]1[CH:38]=[CH:39][C:33]([C:2]2[C:3]([NH2:24])=[N:4][CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@H:16]4[CH2:21][O:20][CH2:19][CH2:18][O:17]4)=[C:10]([O:22][CH3:23])[CH:9]=3)[CH:7]=2)=[CH:34][CH:35]=1
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참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 867000583-Bromo-5-{4-[(2R)-1,4-dioxan-2-ylmethoxy]-3-methoxyphenyl}pyridin-2-amine

생성물 1

HCID 867000573-(4-Aminophenyl)-5-{4-[(2R)-1,4-dioxan-2-ylmethoxy]-3-methoxyphenyl}pyridin-2-amine수율 60.1%

시약·촉매·용매 4

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매
HCID 6212Chloroform용매
HCID 312751,4-Dioxane용매

실험 절차

The compound obtained in Step 2 of Example 41 (2.05 g), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.14 g), tetrakis(triphenylphosphine)palladium (0.3 g), and potassium carbonate (2.15 g) were suspended in dioxane (30 ml) and water (6 ml), and the suspension was stirred at 100° C. for two hours. After leaving to cool, the reaction solution was diluted with chloroform, followed by washing with water. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [ethyl acetate:hexane=1:1->chloroform:ethanol=19:1 (v/v)] to give 1.27 g of the title compound as a solid.

후처리

  1. customAfter leaving
  2. temperatureto cool
  3. washby washing with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [ethyl acetate:hexane=1:1->chloroform:ethanol=19:1 (v/v)]

출처 및 근거

ORD 기록
ord-fba96663e57a4a37a12a7c48235c44d9
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08933103B2

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