1-Naphthaleneboronic acid → HCID 17780340, compound

HRID 2187653Notes

Reaction equation

HRID 2187653 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]([Cl:10])=[C:8]([C:11]3[NH:12][CH2:13][CH2:14][N:15]=3)[S:7][C:6]=2[CH:16]=1.[C:17]1(B(O)O)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:10][C:9]1[C:5]2[CH:4]=[CH:3][C:2]([C:25]3[C:26]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:22]=[CH:23][CH:24]=3)=[CH:16][C:6]=2[S:7][C:8]=1[C:11]1[NH:12][CH2:13][CH2:14][N:15]=1

Participants

6

Reactant 2

HCID 2545321-Naphthaleneboronic acidHCID 18476172HCID 18476172, compound

Product 1

HCID 17780340HCID 17780340, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 60 mg (0.19 mmol) of 2-(6-bromo-3-chlorobenzo[b]thiophen-2-yl)-4,5dihydro-1H-imidazole, 69 mg (0.4 mmol) of naphthalene-1-boronic acid, and 23 mg (0.02 mmol) of Pd(PPh3)4 in a mixture of 2.5 ml dioxane and 0.4 ml 2M aqueous sodium carbonate solution was heated at 95° C. for 24 h. After cooling it was concentrated to dryness under reduced pressure, and the title compound was obtained from the residue by column chromatography on silica gel with dichloromethane/ethanolic ammonia gradient.

Workup

  1. temperatureAfter cooling it
  2. concentrationwas concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ad777f6900904ae887edec52d7b33481
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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