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

HRID 1428106Notes

Reaction equation

HRID 1428106 reaction equation
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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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)]

Sources & evidence

ORD record
ord-fba96663e57a4a37a12a7c48235c44d9
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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