1,3-Propanediol → HCID 11371743, compound

HRID 644507Notes

Reaction equation

HRID 644507 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:20]=[C:19](I)[C:9]2[N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]=[N:12][C:8]=2[CH:7]=1)=[O:5])[CH3:2].[NH2:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1.C(O)CCO.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:22][C:23]1[CH:28]=[C:27]([C:19]2[C:9]3[N:10]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:11]=[N:12][C:8]=3[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:20]=2)[CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 922693-Aminophenylboronic acidHCID 67485000HCID 67485000, compound

Product 1

HCID 11371743HCID 11371743, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

This was prepared analogously to the above product from 5-ethoxycarbonyl-7-iodo-1-phenylbenzimidazole (2.1 g, 5.36 mmol), 3-aminophenylboronic acid (1.1 g, 8.04 mmol), 1,3-propanediol (1.9 ml, 26.8 mmol), potassium carbonate (3.7 g, 26.8 mmol) and bis(triphenylphosphin)palladium dichloride (50 mg, 0.07 mmol) in a mixture of dimethoxyethane (10 ml) and water (5 ml). The title product was obtained as an off-white solid (1.30 g, 68%) m/z, 358.2 (M+H)+.

Sources & evidence

ORD record
ord-7a6a299ae5f34812a7d997dbd993e9e1
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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