Tolylboronic acid → 1,4-Bis[5-(4-methylphenyl)-2-pyridyl]hexahydro-1,4-diazepine

HRID 49290Notes

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.[CH3:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>>[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([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:26]5[CH:27]=[CH:28][C:23]([CH3:22])=[CH:24][CH:25]=5)=[CH:17][N:16]=4)[CH2:10][CH2:9]3)=[N:6][CH:7]=2)=[CH:25][CH:24]=1

Participants

Reactant 2

HCID 79799Tolylboronic acid

HCID 129915931,4-Bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepine

Product 1

HCID 129915981,4-Bis[5-(4-methylphenyl)-2-pyridyl]hexahydro-1,4-diazepineYield 42.8%

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-methylphenylboronic acid (163.0 mg, 1.20 mmol). The crude crystals were recrystallized from chloroform-hexane to yield the title compound as pale yellow needles (melting point: 245.0-247.0° C.)(93.0 mg, yield: 42%).

Workup

customThe crude crystals were recrystallized from chloroform-hexane

Sources & evidence

ORD record: ord-b7d77866183941db9012d90e0a4e417a
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706703B2

Reaction notes

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