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6-Bromo-2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-5′-methylspiro[chroman-4,2′-imidazol]-4′-amine

6-bromo-2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-5′-methylspiro[chroman-4,2′-imidazol]-4′-amine

mixture 1

6-bromo-2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-5′-methylspiro[chroman-4,2′-imidazol]-4′-amine

3-chlorophenylboronic acid

K2CO3

1,4-dioxane

→

title compound

수율 68.5%

6-(3-Chlorophenyl)-2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-5′-methylspiro[chroman-4,2′-imidazol]-4′-amine

수율 68.5%

mixture 1

6-bromo-2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-5′-methylspiro[chroman-4,2′-imidazol]-4′-amine

용매

DCM

반응 조건

후처리

1. 1
   온도When cooled to r.t. the mixture
2. 2
   세척washed with water
3. 3
   건조dried over Na2SO4
4. 4
   농축The filtrate was concentrated
5. 5
   기타the product purified by preparative chromatography

실험 절차

6-Bromo-2-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-5′-methylspiro[chroman-4,2′-imidazol]-4′-amine (Isomeric mixture 1 from Example 49 Step 4, 0.08 g, 0.20 mmol), 3-chlorophenylboronic acid (0.046 g, 0.30 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.015 g, 0.02 mmol), 2 M aq. K2CO3 solution (0.197 mL, 0.39 mmol) and 1,4-dioxane (1.5 mL) were mixed in a vial and heated in a microwave reactor at 130° C. for 20 min. When cooled to r.t. the mixture was diluted with DCM, washed with water and dried over Na2SO4. The filtrate was concentrated and the product purified by preparative chromatography to yield Isomeric mixture 1 of the title compound (30 mg, 35% yield): 1H NMR (500 MHz, CDCl3) δ ppm 1.28 (m, 7H), 1.48 (m, 3H), 1.64 (d, 1H), 1.91 (t, 1H), 2.11 (m, 1H), 2.40 (s, 3H), 2.51 (t, 1H), 3.74 (td, 1H), 3.85 (td, 1H), 4.48 (dd, 1H), 6.81 (d, 1H), 7.01 (d, 1H), 7.26 (m, 1H), 7.32 (d, 2H), 7.40 (m, 2H); MS (ES+) m/z 438 [M+H]+.

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