4-(Trifluoromethyl)phenylboronic acid → 1,4-Bis[5-(4-trifluoromethylphenyl)-2-pyridyl]hexahydro-1,4-diazepine

HRID 49292Notes

Reaction equation

HRID 49292 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]3[CH:20]=[CH:19][C:18](Br)=[CH:17][N:16]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>>[F:22][C:23]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:14][CH2:13][CH2:12][N:11]([C:15]4[CH:20]=[CH:19][C:18]([C:27]5[CH:28]=[CH:29][C:24]([C:23]([F:34])([F:33])[F:22])=[CH:25][CH:26]=5)=[CH:17][N:16]=4)[CH2:10][CH2:9]3)=[N:6][CH:7]=2)=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 129915931,4-Bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepine

Product 1

HCID 129916001,4-Bis[5-(4-trifluoromethylphenyl)-2-pyridyl]hexahydro-1,4-diazepineYield 40.6%

Procedure

Following the procedure of Example 1, crude crystals were obtained from the 1,4-bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepine (206.0 mg, 0.500 mmol) synthesized in Reference Example 1 and 4-trifluoromethylphenylboronic acid (227.0 mg, 1.20 mmol). The crude crystals were recrystallized from chloroform-hexane to yield the title compound as colorless needles (melting point: 236.0-238.0° C.) (110.0 mg, yield: 40%).

Workup

  1. customThe crude crystals were recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-8aa186d4bfdb427a81e4c07c4e8d5722
Source dataset
uspto-grants-2004_03
Patent number
US06706703B2

Reaction notes

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