1-(4-(4-aMino-3-Methoxyphenyl)piperazin-1-yl)ethanone → HCID 68593169, compound
Reaction equation
COc1cc(N2CCN(C(C)=O)CC2)ccc1N.Cc1cnc(Cl)nc1-c1cn(S(=O)(=O)c2ccccc2)c2ccccc12>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]>COc1cc(N2CCN(C(C)=O)CC2)ccc1Nc1ncc(C)c(-c2cn(S(=O)(=O)c3ccccc3)c3ccccc23)n1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 90 °C
Procedure
Cesium carbonate (2.55 g, 7.82 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.301 g, 0.52 mmol) and diacetoxypalladium (0.058 g, 0.26 mmol) were added to a stirred suspension of 3-(2-chloro-5-methylpyrimidin-4-yl)-1-(phenylsulfonyl)-1H-indole (2 g, 5.21 mmol) and 1-(4-(4-amino-3-methoxyphenyl)piperazin-1-yl)ethanone (1.299 g, 5.21 mmol) in 1,4-dioxane (50 ml). The resulting suspension was degassed with argon and stirred at 90 °C for 2 hours. After cooling, the mixture was filtered through a pad of Dicalite speed plus and washed with dichloromethane. The solvent were evaporated. PBO-01132-93-01 The crude product was purified by flash chromatography on silica gel (Merck cartrige SVP D40 - SI60 16-40µm - 90g) eluting with 0 up to 100% EtOAc in dichloromethane . The 1-(4-(3-methoxy-4-(5-methyl-4-(1-(phenylsulfonyl)-1H-indol-3-yl)pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (1.760 g, 56.6 %) was obtained as a yellow oil. PBO-01132-93-02 An impure batch was obtained. PBO-01132-93-03
Sources & evidence
- ORD record
- ord-7e36385bcc0c400fb6d43f0b2d0257ca
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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