1-Bromo-4-(methylsulphonyl)benzene → tert-butyl (2R)-2-methyl-4-(4-methylsulfonylphenyl)piperazine-1-carboxylate

HRID 691

Reaction equation

HRID 691 reaction equation
CS(=O)(=O)c1ccc(Br)cc1.C[C@@H]1CNCCN1C(=O)OC(C)(C)C>C1COCCO1.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)[O-].[K+].[Pd]>C[C@@H]1CN(c2ccc(S(C)(=O)=O)cc2)CCN1C(=O)OC(C)(C)C

Participants

7

Reactant 2

HCID 770141-Bromo-4-(methylsulphonyl)benzeneHCID 10262201tert-Butyl (2R)-2-methylpiperazine-1-carboxylate

Product 1

HCID 133499578tert-butyl (2R)-2-methyl-4-(4-methylsulfonylphenyl)piperazine-1-carboxylateYield 0%

Reagents, catalysts & solvents 4

HCID 23665647Potassium tert-butoxideReagentHCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

13-May-09 10:32:28 +0100 1-bromo-4-(methylsulfonyl)benzene (515 mg, 2.13 mmol), (R)-tert-butyl 2-methylpiperazine-1-carboxylate (426 mg, 2.13 mmol) and BIS(TRI-T- BUTYLPHOSPHINE)PALLADIUM(0) (54.3 mg, 0.11 mmol) and potassium 2-methylpropan-2-olate (352 mg, 2.98 mmol) were suspended in dioxane (10 mL) and heated to 90°C for 3 hours. LC-MS shows starting material. Reaction abandoned.

Sources & evidence

ORD record
ord-8f20cf3b966d4cdd9e1178539b8e969e
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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