Phenylboronic Acid → 4-(2-Methoxyphenyl)-1-{3-[5-methyl-2-(4-phenylphenyl)-1H-indol-3-yl]-1-oxopropyl}piperazine

HRID 1058971

Reaction equation

HRID 1058971 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])[CH2:23][CH2:22]2)=[O:20])=[CH:14][C:13]([CH3:35])=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.[C:36]1(B(O)O)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH3:34][O:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[N:24]1[CH2:25][CH2:26][N:21]([C:19](=[O:20])[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH3:35])[CH:14]=3)[NH:9][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:3][CH:4]=2)[CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 4896623-[2-(4-bromophenyl)-5-methyl-1H-indol-3-yl]-1-[4-(2-methoxyphenyl)piperazin-1-yl]propan-1-one

Product 1

HCID 186690854-(2-Methoxyphenyl)-1-{3-[5-methyl-2-(4-phenylphenyl)-1H-indol-3-yl]-1-oxopropyl}piperazine

Procedure

Prepared from 1-{3-[2-(4-bromophenyl)-5-methyl-1H-indol-3-yl]-1-oxopropyl}-4-(2-methoxyphenyl)piperazine (Example 1) and phenylboronic acid according to the method of Example 117. 1H NMR (360 MHz, CDCl3) δ8.05 (1H, br s), 7.71-7.61 (6H, m), 7.48-7.44 (3H, m), 7.39-7.35 (1H, m), 7.29-7.25 (1H, m), 7.06-6.98 (2H, m), 6.90-6.77 (3H, m), 3.82 (3H, s), 3.78 (2H, t, J 5.0 Hz), 3.46 (2H, t, J 5.0 Hz), 3.33 (2H, m), 2.92 (2H, t, J 5.0 Hz), 2.74 (4H, m), and 2.48 (3H, s). m/z (ES+) 530 (M+1).

Sources & evidence

ORD record
ord-cddcd264c5fb495d9e93be503dfbb7a9
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Linked notes

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