吗啉 → 2,6-dimethyl-N-[(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)-(4-morpholin-4-ylphenyl)methyl]benzamide

HRID 263笔记

反应方程式

HRID 263 反应方程式
C1COCCN1.Cc1cccc(C)c1C(=O)NC(c1ccc(Br)cc1)C12CCC(CC1)N2C>CC(=O)O.CC(=O)O.CC(C)(C)[O-].CN(C)C=O.[K+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>Cc1cccc(C)c1C(=O)NC(c1ccc(N2CCOCC2)cc1)C12CCC(CC1)N2C

参与物

7

反应物 2

HCID 8083吗啉HCID 46863192N-[(4-bromophenyl)-(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)methyl]-2,6-dimethylbenzamide

产物 1

HCID 468633132,6-dimethyl-N-[(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)-(4-morpholin-4-ylphenyl)methyl]benzamide收率 29.57%

试剂、催化剂与溶剂 4

HCID 23665647叔丁醇钾试剂HCID 634876R-(+)-1,1'-联萘-2,2'-双二苯膦催化剂HCID 4144353醋酸钯催化剂HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
130 °C

实验过程

In a CEM microwave vial was N-((4-bromophenyl)(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)methyl)-2,6-dimethylbenzamide (100 mg, 0.23 mmol), morpholine (0.082 mL, 0.94 mmol), palladium(II) acetate (5.25 mg, 0.02 mmol), BINAP (14.57 mg, 0.02 mmol), and potassium tert-butoxide (52.5 mg, 0.47 mmol) solid and DMF (2 mL) was added. The vial was capped and placed into the microwave at 300 watts, 130 °C for 4 minutes. After reaction completion, the the mixture was concentrated and crude taken up in CH2Cl2 and washed with water and dried (Na2SO4). The material was purified on a 12 gram Isco silica cartridge and eluted with 0% to 5% MeOH 2M NH3/CH2Cl2 to give a light yellowish solid 2,6-dimethyl-N-((7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)(4-morpholinophenyl)methyl)benzamide (30.0 mg, 29.6 %).

来源与证据

ORD记录
ord-ea53d8feb8094f94b89810756f770f19
来源数据集
750 AstraZeneca ELN dataset
原始链接
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反应笔记

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