1,3-Propanediol → HCID 11303270, compound

HRID 644508Notes

Reaction equation

HRID 644508 reaction equation
C(N[C:5]1[CH:6]=[C:7]([C:11]2[C:16]3[N:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:18]=[N:19][C:15]=3[CH:14]=[C:13]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=O)C.[CH2:31]([O:33]C(C1C=C(I)C2N(C3C=CC=CC=3)C=NC=2C=1)=O)C.OCC1C=C(B(O)O)C=CC=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>[CH2:29]([O:28][C:26]([C:13]1[CH:12]=[C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([CH2:31][OH:33])[CH:6]=2)[C:16]2[N:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:18]=[N:19][C:15]=2[CH:14]=1)=[O:27])[CH3:30]

Participants

9

Reactant 5

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 11153793HCID 11153793, compoundHCID 67485000HCID 67485000, compound

Product 1

HCID 11303270HCID 11303270, compound

Reagents, catalysts & solvents 3

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

Procedure

This was prepared analogously to 7-(3-acetamidophenyl)-5-ethoxycarbonyl-1-phenylbenzimidazole from 5-ethoxycarbonyl-7-iodo-1-phenylbenzimidazole (2.7 g, 6.89 mmol), 3-(hydroxymethyl)phenylboronic acid (1.57 g, 10.3 mmol), 1,3-propanediol (2.5 ml, 34.4 mmol), potassium carbonate (4.75 g, 34.4 mmol) and bis(triphenylphosphin)palladium dichloride (100 mg, 0.14 mmol) in a mixture of dimethoxyethane (30 ml) and water (15 ml). The title product was obtained as an off-white solid (2.1 g, 82%) m/z, 373.2 (M+H)+.

Sources & evidence

ORD record
ord-b138783261f743bd822a537a35dd8f59
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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