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N,N-Dimethylethylenediamine → N-(4-bromo-3-methoxyphenyl)-N',N'-dimethylethane-1,2-diamine

HRID 649
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HRID 649 반응식
CN(C)CCN.COc1cc(I)ccc1Br>CC(C)(C)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd]>COc1cc(NCCN(C)C)ccc1Br
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참가 물질

7

반응물 2

HCID 66053N,N-DimethylethylenediamineHCID 121872021-Bromo-4-iodo-2-methoxybenzene

생성물 1

HCID 82868020N-(4-bromo-3-methoxyphenyl)-N',N'-dimethylethane-1,2-diamine수율 45.64%

시약·촉매·용매 4

HCID 23676156Sodium t-butoxide시약HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매
HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 1140Toluene용매

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온도
80 °C

실험 절차

A solution of 1-bromo-4-iodo-2-methoxybenzene (0.63 g, 2.01 mmol) dissolved in toluene (15.73 ml) was treated with N1,N1-dimethylethane-1,2-diamine (0.177 g, 2.01 mmol), SODIUM TERT-BUTOXIDE (0.232 g, 2.42 mmol), XANTPHOS (0.116 g, 0.20 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.046 g, 0.05 mmol) under nitrogen. The resulting mixture was stirred at 80 °C in a sealed tube for 2 hours. The reaction mixture was diluted with water (200 mL), and extracted with ethyl acetate (200 mL). The organic was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution 0-10% methanol in dcm. Pure fractions were evaporated to dryness to afford N1-(4-bromo-3-methoxyphenyl)-N2,N2-dimethylethane-1,2-diamine (0.251 g, 45.6 %) as a brown oil.

출처 및 근거

ORD 기록
ord-a7c71c7b356644fcbb6f6b90814539ca
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
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