4-tert-Butylphenylboronic acid → 1,4-Bis[5-(4-t-butylphenyl)-2-pyridyl]hexahydro-1,4-diazepine

HRID 49291

Reaction equation

HRID 49291 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.[C:22]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>>[C:22]([C:26]1[CH:31]=[CH:30][C:29]([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:29]5[CH:30]=[CH:31][C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:27][CH:28]=5)=[CH:17][N:16]=4)[CH2:10][CH2:9]3)=[N:6][CH:7]=2)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 27343204-tert-Butylphenylboronic acidHCID 129915931,4-Bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepine

Product 1

HCID 129915991,4-Bis[5-(4-t-butylphenyl)-2-pyridyl]hexahydro-1,4-diazepineYield 45.1%

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-t-butylphenylboronic acid (226.0 mg, 1.20 mmol). The crude crystals were recrystallized from chloroform-hexane to yield the title compound as colorless needles (melting point: 268.0-270.0° C.) (117.0 mg, yield: 42%).

Workup

  1. customThe crude crystals were recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-96b60b7afc914f32b96110c2fcb78aa9
Source dataset
uspto-grants-2004_03
Patent number
US06706703B2

Linked notes

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