Hydrochloric Acid → HCID 24874652, compound

HRID 2264747Notes

Reaction equation

HRID 2264747 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([CH3:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:17])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[C:24]([Cl:26])[CH:25]=1.Cl>ClCCl>[ClH:19].[Cl:19][C:20]1[CH:21]=[C:22]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3([CH3:18])[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:10]([NH2:17])=[N:9]3)[CH:3]=2)[CH:23]=[C:24]([Cl:26])[CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 27343313,5-Dichlorophenylboronic acidHCID 595962321-(3-Bromophenyl)-1-methyl-1H-isoindol-3-amine

Product 1

HCID 24874652HCID 24874652, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described for Example 78 (Scheme #14, N) starting from 1-(3-bromophenyl)-1-methyl-1H-isoindol-3-amine (Example 90) (71.4 mg, 0.237) and (3,5-dichlorophenyl)boronic acid (47.4 mg, 0.249 mmol) with the exception that the hydrochloride was made by dissolving the product in dichloromethane (1 mL) and adding hydrochloric acid (0.71 mL, 1 M in diethyl ether). The solution was stirred for 1 h and was then concentrated to afford 31.0 mg (32% yield) of the title compound: 1H NMR (DMSO-d6) δ 8.23 (d, J=7.78 Hz, 1 H), 7.91-7.87 (m, 1 H), 7.84-7.74 (m, 4 H), 7.71 (d, J=7.78 Hz, 1 H), 7.67-7.62 (m, 2 H), 7.47 (t, J=7.78 Hz, 1 H), 7.43-7.38 (m, 1 H), 2.06 (s, 3 H); MS (ES) m/z 367, 369, 371 [M+1]+.

Workup

  1. customThe title compound was prepared
  2. concentrationwas then concentrated

Sources & evidence

ORD record
ord-21b09bfff11c4c65a2d8b65840d679d0
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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