4-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile → 3'-(3-Amino-1-cyclopropyl-1H-isoindol-1-yl)-5-methoxybiphenyl-2-carbonitrile acetate

HRID 2264745Notes

Reaction equation

HRID 2264745 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].Br[C:6]1[CH:7]=[C:8]([C:12]2([CH:22]3[CH2:24][CH2:23]3)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([NH2:21])=[N:13]2)[CH:9]=[CH:10][CH:11]=1.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=1>>[C:1]([OH:4])(=[O:3])[CH3:2].[NH2:21][C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([C:8]2[CH:7]=[C:6]([C:33]3[C:30]([C:31]#[N:32])=[CH:29][CH:28]=[C:27]([O:26][CH3:25])[CH:34]=3)[CH:11]=[CH:10][CH:9]=2)([CH:22]2[CH2:23][CH2:24]2)[N:13]=1

Participants

3

Reactant 2

HCID 597640214-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileHCID 672723191-(3-Bromophenyl)-1-cyclopropyl-1H-isoindol-3-amine acetate

Product 1

HCID 248746463'-(3-Amino-1-cyclopropyl-1H-isoindol-1-yl)-5-methoxybiphenyl-2-carbonitrile acetateYield 51%

Procedure

The title compound was prepared in 51% yield as described for Example 78 (Scheme #14, N) starting from 1-(3-bromophenyl)-1-cyclopropyl-1H-isoindol-3-amine acetate (Scheme #15, O) and 4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile: 1H NMR (DMSO-d6) δ 7.89-7.84 (m, 2 H), 7.75-7.68 (m, 1 H), 7.68-7.63 (m, 1 H), 7.56-7.51 (m, 1 H), 7.43-7.35 (m, 4 H), 7.12 (dd, J=8.66, 2.64 Hz, 1 H), 7.06 (d, J=2.51 Hz, 1 H), 3.89 (s, 3 H), 1.92-1.83 (m, 4 H), 0.49-0.38 (m, 2 H), 0.25-0.16 (m, 1 H), −0.04-0.03 (m, 1 H): MS (ES) m/z 380 [M+1]+.

Sources & evidence

ORD record
ord-b5013f2e8b9041bcb83ee2fbd49ea144
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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