(Pyrimidin-5-yl)boronic acid → 1-Isopropyl-1-(3-pyrimidin-5-ylphenyl)-1H-isoindol-3-amine acetate

HRID 2264748Notes

Reaction equation

HRID 2264748 reaction equation
Cl.Br[C:3]1[CH:4]=[C:5]([C:9]2([CH:19]([CH3:21])[CH3:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:18])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.[C:22]([OH:25])(=[O:24])[CH3:23].BrC1C=[C:29]([C:33]2(C(C)C)C3C(=CC=CC=3)[C:35]([NH2:42])=[N:34]2)[CH:30]=CC=1.N1C=C(B(O)O)C=NC=1>>[C:22]([OH:25])(=[O:24])[CH3:23].[CH:19]([C:9]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:29]3[CH:33]=[N:34][CH:35]=[N:42][CH:30]=3)[CH:4]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([NH2:18])=[N:10]1)([CH3:21])[CH3:20]

Participants

4

Reactant 3

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 672723581-(3-Bromophenyl)-1-isopropyl-1H-isoindol-3-amine acetateHCID 672730831-(3-Bromophenyl)-1-isopropyl-1H-isoindol-3-amine hydrochloride

Product 1

HCID 672731091-Isopropyl-1-(3-pyrimidin-5-ylphenyl)-1H-isoindol-3-amine acetateYield 81%

Procedure

The title compound was prepared as described for Example 78 (Scheme #14, N) starting from 1-(3-bromophenyl)-1-isopropyl-1H-isoindol-3-amine hydrochloride (Example 89, Scheme #16, P) (15.0 mg, 0.0410 mmol), 1-(3-bromophenyl)-1-isopropyl-1H-isoindol-3-amine acetate (Scheme #17, Q) (6.5 mg, 0.0167 mmol) and pyrimidine-5-ylboronic acid (15.9 mg, 0.128 mmol) to give 18.2 mg (81% yield): 1H NMR (DMSO-d6) δ 9.19 (d, J=2.14 Hz, 1 H), 9.10 (d, J=2.14 Hz, 2 H), 8.06 (d, J=1.23 Hz, 1 H), 7.85 (d, J=8.58 Hz, 1 H), 7.73 (t, J=9.19 Hz, 2 H), 7.62 (d, J=7.66 Hz, 1 H), 7.48-7.31 (m, 3 H), 3.02-2.91 (m, 1 H), 1.89 (s, 3 H), 0.86 (d, J=6.74 Hz, 3 H), 0.43 (d, J=6.43 Hz, 3H); MS (ES) m/z 329 [M+1]+.

Workup

  1. customto give 18.2 mg (81% yield)

Sources & evidence

ORD record
ord-f65c0c0e25344027b1ea961bd34c5801
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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