Dichloromethane → 1-Methyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)piperazine

HRID 2097262Notes

Reaction equation

HRID 2097262 reaction equation
C(Cl)Cl.Br[C:5]1[CH:6]=[C:7]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1.CCN(CC)CC.[CH3:25][C:26]1([CH3:33])[C:30]([CH3:32])([CH3:31])[O:29][BH:28][O:27]1>C1(C)C=CC=CC=1.Cl[Pd]Cl>[CH3:17][N:14]1[CH2:15][CH2:16][N:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([B:28]3[O:29][C:30]([CH3:32])([CH3:31])[C:26]([CH3:33])([CH3:25])[O:27]3)[CH:6]=2)[CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 534153291-(3-Bromophenyl)-4-methylpiperazine

Product 1

HCID 592647461-Methyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)piperazine

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of PdCl2 (dppf).DCM (10 mg, 0.012 mmol) in anhydrous toluene (4 ml) in an argon filled sealed microwave tube was added the 1-(3-Bromo-phenyl)-4-methyl-piperazine (100 mg, 0.39 mmol), Et3N (0.11 ml, 2 equiv.), and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.09 ml, 1.5 equiv). The microwave tube was evacuated and backfilled with Argon before being irradiated in a CEM Microwave reactor at 100° C. for 1 hr using an initial power of 200 W. The reaction mixture was partitioned between more toluene (6 ml) and water (10 ml), the organic layer separated, washed with water (1×10 ml), dried over MgSO4 and then evaporated in vacuo to leave a purple/brown residue which was used for suzuki coupling without further purification.

Workup

  1. customsealed microwave tube
  2. customThe microwave tube was evacuated
  3. custombefore being irradiated in a CEM Microwave reactor at 100° C. for 1 hr
  4. customThe reaction mixture was partitioned between more toluene (6 ml) and water (10 ml)
  5. customthe organic layer separated
  6. washwashed with water (1×10 ml)
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuo
  9. customto leave a purple/brown residue which
  10. customwas used for suzuki coupling without further purification

Sources & evidence

ORD record
ord-40380ed623684c7297f5c9b8311f148e
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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