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1-Methylpiperazine → Methyl 3-(4-methyl-1-piperazinyl)-5-nitrobenzoate

HRID 719
ノート
印刷プレビュー

反応式

HRID 719 の反応式
CN1CCNCC1.COC(=O)c1cc(Br)cc([N+](=O)[O-])c1>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>COC(=O)c1cc(N2CCN(C)CC2)cc([N+](=O)[O-])c1
参加物反応条件実験手順出典と根拠反応ノート

参加物

7

反応物 2

HCID 531671-MethylpiperazineHCID 239341Methyl 3-bromo-5-nitrobenzoate

生成物 1

HCID 67513628Methyl 3-(4-methyl-1-piperazinyl)-5-nitrobenzoate収率 65.18%

試薬・触媒・溶媒 4

HCID 10796Cesium carbonate試薬HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒
HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

To the stirred suspension ofmethyl 3-bromo-5-nitrobenzoate (2 g, 7.69 mmol) , cesium carbonate (12.53 g, 38.46 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.111 g, 0.19 mmol) in Dioxane (12 mL) (degassed with N2) was added pd (dba)3 (0.176 g, 0.19 mmol) and cesium carbonate (12.53 g, 38.46 mmol) AND rxn was heated at 110 ºC for 1 hr in microwaved. LCMS showed the m+1= 280. The crude raection mixture was filtered over celite. The filtrate was concentarted. The crude solid was diluted by 20 mL ethyl acetate, washed with 3x10 mL water, brine, collected the organic layers, concentrated. The crude solid was added to a silica gel column and was eluted with 0-10% methanol in DCM. Collected desired fractions. Obtained=1.4 gm. 1H NMR (300 MHz, DICHLOROMETHANE- _d_ 2) d ppm 2.32 (s, 3 H) 2.43 - 2.64 (m, 4 H) 3.13 - 3.40 (m, 4 H) 3.93 (s, 3 H) 7.85 (d, _J_ =1.70 Hz, 2H) 8.18 (t, _J_ =1.60 Hz, 1 H) Registered as AZ13477915.

出典と根拠

ORDレコード
ord-0986b91ec7734959810ebeac46571d3f
出典データセット
750 AstraZeneca ELN dataset
元リンク
出典を表示

反応ノート

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