Tetrafluoroborate → HCID 44456312, compound

HRID 1454226Notes

Reaction equation

HRID 1454226 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:15]=[C:14]([C:16]([N:18]2[CH2:23][CH2:22][N:21]([CH:24]([CH3:26])[CH3:25])[CH2:20][CH2:19]2)=[O:17])[CH:13]=[CH:12][C:11]=1[O:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=1)C)(C)(C)C.C(OC(=O)NCC1C=C(Br)C=CC=1OC1C=CC(Cl)=C(Cl)C=1)(C)(C)C.C1CCN2C(=NCCC2)CC1.C(N1CCNCC1)(C)C.F[B-](F)(F)F>C1COCC1>[Cl:35][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][C:31]=1[Cl:34])[O:27][C:11]1[CH:12]=[CH:13][C:14]([C:16]([N:18]2[CH2:19][CH2:20][N:21]([CH:24]([CH3:25])[CH3:26])[CH2:22][CH2:23]2)=[O:17])=[CH:15][C:10]=1[CH2:9][NH:7][CH3:6]

Participants

7

Reactant 5

HCID 26255TetrafluoroborateHCID 780131-IsopropylpiperazineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68848219HCID 68848219, compoundHCID 68852117HCID 68852117, compound

Product 1

HCID 44456312HCID 44456312, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[2-(3,4-Dichloro-phenoxy)-5-(4-isopropyl-piperazine-1-carbonyl)-benzyl]-methyl-carbamic acid tert-butyl ester. To a solution of [5-bromo-2-(3,4-dichloro-phenoxy)-benzyl]-carbamic acid tert-butyl ester (327.0 mg, 0.71 mmol) in THF (2 mL) were added DBU (0.30 mL, 2.0 mmol), 1-isopropyl piperazine (0.30 mL, 2.5 mmol), Hermann's catalyst (31.9 mg, 0.034 mmol), tri-t-butylphosphium tetrafluoroborate (26.4 mg, 0.091 mmol), and Mo(CO)6 (211.0 mg, 0.80 mmol). After 6 min in a microwave reactor at 125° C., the mixture was cooled to rt and concentrated. Purification by FCC gave the desired product (212.5 mg, 56%).

Workup

  1. concentrationconcentrated
  2. customPurification by FCC

Sources & evidence

ORD record
ord-255c79a53673427c96c0b727c1e36d15
Source dataset
uspto-grants-2009_01
Patent number
US07479493B2

Reaction notes

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