Methyl 3-hydroxy-4,5-dimethoxybenzoate → 1,4-Bis[5-(3-benzyloxy-4,5-dimethoxyphenyl)-2-pyridyl]hexahydro-1,4-diazepine

HRID 460388Notes

Reaction equation

HRID 460388 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.[CH2:22]([O:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[C:34]([O:38][CH3:39])[C:35]=1[O:36][CH3:37])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH:43][C:44]1[CH:45]=[C:46]([CH:51]=[C:52]([O:56][CH3:57])[C:53]=1[O:54][CH3:55])C(OC)=O>>[CH2:22]([O:29][C:30]1[CH:31]=[C:32]([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:46]5[CH:51]=[C:52]([O:56][CH3:57])[C:53]([O:54][CH3:55])=[C:44]([O:43][CH2:22][C:23]6[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=6)[CH:45]=5)=[CH:17][N:16]=4)[CH2:10][CH2:9]3)=[N:6][CH:7]=2)[CH:33]=[C:34]([O:38][CH3:39])[C:35]=1[O:36][CH3:37])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 2733956Methyl 3-hydroxy-4,5-dimethoxybenzoateHCID 129915931,4-Bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepineHCID 20634994(3-(Benzyloxy)-4,5-dimethoxyphenyl)boronic acid

Product 1

HCID 206349611,4-Bis[5-(3-benzyloxy-4,5-dimethoxyphenyl)-2-pyridyl]hexahydro-1,4-diazepine

Procedure

The procedure described in Example 31 was employed. From 1,4-bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepine (115.0 mg, 0.280 mmol) synthesized in Reference Example 1 and 3-benzyloxy-4,5-dimethoxyphenylboronic acid (170.0 mg, 0.590 mmol) synthesized from methyl 3-hydroxy-4,5-dimethoxybenzoate (Indian J. Chem., 21B, 27–29, (1982)) by a similar procedure to that described in Reference Example 8, 1,4-bis[5-(3-benzyloxy-4,5-dimethoxyphenyl)-2-pyridyl]hexahydro-1,4-diazepine was obtained as a colorless viscous oil (173.0 mg, yield: 84%). From 1,4-bis[5-(3-benzyloxy-4,5-dimethoxyphenyl)-2-pyridyl]hexahydro-1,4-diazepine (157.0 mg, 0.210 mmol), 1,4-bis[5-(3-hydroxy-4,5-dimethoxyphenyl)-2-pyridyl]-hexahydro-1,4-diazepine was obtained as a colorless oil (97.0 mg, yield: 84%).

Sources & evidence

ORD record
ord-34eb7ea1269148b5a1c2f1dff683d731
Source dataset
uspto-grants-2007_03
Patent number
US07196101B2

Reaction notes

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