Boric Acid → Methyl 2-(1-methyl-3-indolyl)-6-benzoxazolylacetate

HRID 1372636Notes

Reaction equation

HRID 1372636 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=O)=[CH:3]1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][C:16]=1O.B(O)(O)O>C1(C)C(C)=CC=CC=1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[O:13][C:16]3[CH:17]=[C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:20][C:15]=3[N:14]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 7628Boric AcidHCID 8540401-Methylindole-3-carboxylic acidHCID 17858854Methyl 2-(4-amino-3-hydroxyphenyl)acetate

Product 1

HCID 58778404Methyl 2-(1-methyl-3-indolyl)-6-benzoxazolylacetateYield 11%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In xylene (20 mL), a mixture of 1-methyl-3-indolecarboxylic acid (1.00 g, 5.71 mmol), methyl 4-amino-3-hydroxyphenylacetate (1.03 g, 5.71 mmol) and boric acid (1.05 g, 17.1 mmol) was heated and refluxed for 24 hours by using a Dean-Stark trap. After the reaction mixture was cooled down to room temperature, the solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column, whereby from chloroform-ethyl acetate (4:1, v/v) eluate fractions, methyl 2-(1-methyl-3-indolyl)-6-benzoxazolylacetate (0.20 g, 11%) was obtained as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 24 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by chromatography on a silica gel column, whereby from chloroform-ethyl acetate (4:1

Sources & evidence

ORD record
ord-00d7bc3c10d445f8bde9147da2d41bb6
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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