6-(1H-indol-4-yl)-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazole

Base Information

• Chemical Name: 6-(1H-indol-4-yl)-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazole
• CAS No.: 1364802-72-1
• Molecular Formula: C₃₂H₃₂N₆O₃S
• Molecular Weight: 580.71

Synonyms:6-(1H-indol-4-yl)-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazole

Chemical Property of 6-(1H-indol-4-yl)-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazole

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Technology Process of 6-(1H-indol-4-yl)-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazole

There total 16 articles about 6-(1H-indol-4-yl)-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.6%

C24H26BrN5O3S + indole-4-boronic acid pinacol ester (388116-27-6) → 6-(1H-indol-4-yl)-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazole (1364802-72-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium acetate; In N,N-dimethyl-formamide; at 150 ℃; for 10h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;

Reference yield: 82.0%

6-chloro-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazole (1254036-86-6) + indole-4-boronic acid pinacol ester (388116-27-6) → 6-(1H-indol-4-yl)-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazole (1364802-72-1)

Guidance literature:

With potassium dihydrogenphosphate; potassium hydrogen bifluoride; palladium diacetate; tricyclohexylphosphine; In water; isopropyl alcohol; at 20 - 80 ℃; for 18h; Large scale;

DOI:10.1021/acs.oprd.8b00006

Reference yield:

5-chloro-2-methyl-1,3-dinitro-benzene (35572-79-3) → 6-(1H-indol-4-yl)-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazole (1364802-72-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: diammonium sulfide / water; ethanol

2.1: sodium nitrite

3.1: nickel; hydrazine hydrate

4.1: acetic acid; acetic anhydride

5.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / tetrahydrofuran

6.1: lithium hexamethyldisilazane; zinc(II) chloride / tetrahydrofuran / -10 °C

6.2: 60 °C

7.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / 0 °C

8.1: bromine; triphenylphosphine / dichloromethane

9.1: triethylamine / dimethyl sulfoxide

10.1: palladium diacetate; tricyclohexylphosphine; potassium hydrogenfluoride; potassium phosphate / isopropyl alcohol; water / 80 °C

With diammonium sulfide; potassium phosphate; potassium hydrogenfluoride; bromine; tetra(n-butyl)ammonium hydrogensulfate; palladium diacetate; acetic anhydride; nickel; diisobutylaluminium hydride; hydrazine hydrate; acetic acid; triethylamine; triphenylphosphine; sodium hydroxide; zinc(II) chloride; lithium hexamethyldisilazane; sodium nitrite; tricyclohexylphosphine; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; isopropyl alcohol; toluene; 10.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.oprd.0c00486

upstream raw materials:

4-bromo-1H-indole

benzenesulfonyl chloride

6-chloro-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazole

indole-4-boronic acid pinacol ester

Downstream raw materials:

C₇H₈O₃S*C₂₆H₂₈N₆O

6-(1H-indol-4-yl)-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1H-indazole hydrochloride

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