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Aniline → 4-chloro-N-phenylpyridin-2-amine

HRID 65
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인쇄 미리보기

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HRID 65 반응식
Clc1ccnc(Cl)c1.Nc1ccccc1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>Clc1ccnc(Nc2ccccc2)c1
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참가 물질

7

반응물 2

HCID 6115AnilineHCID 335152,4-Dichloropyridine

생성물 1

HCID 234580414-chloro-N-phenylpyridin-2-amine수율 55.82%

시약·촉매·용매 4

HCID 10796Cesium carbonate시약HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 4144353Palladium (II) acetate촉매

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온도
100 °C

실험 절차

diacetoxypalladium (0.303 g, 1.35 mmol) was added in one portion to a degassed mixture of 2,4-dichloropyridine (10 g, 67.57 mmol), aniline (6.29 g, 67.57 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.173 g, 2.03 mmol) and cesium carbonate (44.0 g, 135.14 mmol) in dioxane (250 mL) under argon. The resulting mixture was stirred at 100 °C for 24 hours. The mixture was then cooled to room temperature, filtered and concentrated to dryness to give the crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford 4-chloro-N-phenylpyridin-2-amine (7.72 g, 55.8 %) as a pale orange solid.

출처 및 근거

ORD 기록
ord-203f818b7f344d11a82d6bc3539ff565
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
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HCID 31275
1,4-Dioxane
용매