1,8-Diaminonaphthalene → 2-(3-Chloro-4-fluorophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

HRID 1846049Notes

Reaction equation

HRID 1846049 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([B:9](O)O)[CH:5]=[CH:6][C:7]=1[F:8].[C:12]1([NH2:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[NH2:22])[CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([B:9]2[NH:23][C:12]3[C:21]4[C:16]([CH:15]=[CH:14][CH:13]=3)=[CH:17][CH:18]=[CH:19][C:20]=4[NH:22]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 680671,8-DiaminonaphthaleneHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 867232622-(3-Chloro-4-fluorophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinineYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-chloro-4-fluorobenzene boronic acid (4 g, 22.8 mmol) and naphthalene-1,8-diamine (3.62 g, 22.9 mol) in anhydrous toluene (80 mL) was heated to reflux for 4 hours. The reaction mixture was cooled to room temperature, then concentrated in vacuo. The residue was trituated with hexane to afford the title compound as a grey solid in 88% yield, 6 g.

Workup

  1. temperatureto reflux for 4 hours
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a621e16718ee4da586577ef394c7c1e2
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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