4-Aminobenzyl alcohol → HCID 69055850, compound

HRID 492251Notes

Reaction equation

HRID 492251 reaction equation
[CH:1](N(C(C)C)CC)(C)[CH3:2].[OH:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20]([OH:22])=O)=[CH:14]2.[NH2:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][OH:29])=[CH:26][CH:25]=1.CN(C(ON1N=N[C:42]2[CH:43]=[CH:44][CH:45]=N[C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(OCC)(=O)C.CN(C=O)C>[CH2:41]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20]([NH:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][OH:29])=[CH:26][CH:25]=1)=[O:22])=[CH:14]2)[C:42]1[CH:2]=[CH:1][CH:45]=[CH:44][CH:43]=1

Participants

7

Reactant 4

HCID 693314-Aminobenzyl alcoholHCID 81531DiisopropylethylamineHCID 889585-Hydroxyindole-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 69055850HCID 69055850, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diisopropylethylamine (673 μL) was added to a DMF solution (2.0 mL) of 5-hydroxyindole-2-carboxylic acid (516 mg), 4-amino-benzyl alcohol (262 mg) and HATU (734 mg), and stirred at room temperature for 2.5 hours. The reaction liquid was diluted with ethyl acetate, and the organic layer was washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water. The organic layer was dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was diluted with diethyl ether and the resulting crystal was taken out through filtration to obtain 5-(benzyloxy)-N-[4-(hydroxymethyl)phenyl]-1H-indole-2-carboxamide (541 mg) as a brown solid.

Workup

  1. customThe reaction liquid
  2. washthe organic layer was washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was diluted with diethyl ether
  6. filtrationthe resulting crystal was taken out through filtration

Sources & evidence

ORD record
ord-91bbd5eca8cf4404bea7c50ea0c9892f
Source dataset
uspto-grants-2009_05
Patent number
US07531668B2

Reaction notes

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