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2-Amino-N-methylbenzamide → 2-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide

HRID 29
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HRID 29 반응식
CNC(=O)c1ccccc1N.Clc1cc(I)c(Cl)cn1>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]>CNC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl
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참가 물질

7

반응물 2

HCID 3080722-Amino-N-methylbenzamideHCID 534009652,5-Dichloro-4-iodopyridine

생성물 1

HCID 575168912-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide수율 32.06%

시약·촉매·용매 4

HCID 10796Cesium carbonate시약HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매
HCID 4144353
Palladium (II) acetate
촉매
HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

Palladium(II) acetate (0.098 g, 0.44 mmol) was added to 2,5-dichloro-4-iodopyridine (3 g, 10.95 mmol), 2-amino-N-methylbenzamide (1.645 g, 10.95 mmol), Cesium carbonate (7.14 g, 21.91 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.380 g, 0.66 mmol) in dioxane (150 mL) under nitrogen. The resulting suspension was stirred at 80 °C for 18 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness. The crude residue was triturated with DCM to give a solid which was collected by filtration and dried under vacuum to give 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (1.58 g, 49 %) as a tan solid, LCMS indicated 87% pure. This was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (1.040 g, 32.1 %) as a yellow solid.

출처 및 근거

ORD 기록
ord-36d41d697d8f415b8c7cc3a381080785
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
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