Boric Acid → HCID 58779044, compound

HRID 1372756Notes

Reaction equation

HRID 1372756 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.C(Cl)(=O)C(Cl)=O.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[C:23]([F:32])[C:22]=1O.B(O)(O)O>CN(C=O)C.C(Cl)Cl>[F:32][C:23]1[C:22]2[O:13][C:11]([C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:2]([CH3:1])[CH:3]=3)=[N:20][C:21]=2[CH:26]=[CH:25][C:24]=1[CH2:27][C:28]([O:30][CH3:31])=[O:29]

Participants

7

Reactant 4

HCID 7628Boric AcidHCID 65578Oxalyl chlorideHCID 8540401-Methylindole-3-carboxylic acidHCID 17859032Methyl (4-amino-2-fluoro-3-hydroxyphenyl)acetate

Product 1

HCID 58779044HCID 58779044, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 1-methylindole-3-carboxylic acid (917 mg, 5.23 mmol) was added methylene chloride (20 ml). Under stirring at 0° C., oxalyl chloride (0.68 ml, 7.85 mmol) and DMF (catalytic amount) were added. After stirring at room temperature for 1.5 hours, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was added with xylene (20 ml). Methyl (4-amino-2-fluoro-3-hydroxyphenyl)acetate (1.0 g, 5.0 mmol) and boric acid (539 mg, 8.72 mmol) were added to the resulting mixture, followed by stirring at 160° C. for 3 days. After the reaction mixture was cooled to room temperature, ice water was added thereto, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was subjected to chromatography on a silica gel column to collect chloroform/ethyl acetate (10/1) eluate fractions and then, purified by chromatography using a thin layer plate, whereby from chloroform/acetone (10/1) eluate fractions, methyl 7-fluoro-2-(1-methyl-3-indolyl)-6-benzoxazolylacetate (62 mg, 4%) was obtained as a pale brown solid.

Workup

  1. stirringAfter stirring at room temperature for 1.5 hours
  2. distillationthe reaction mixture was distilled under reduced pressure
  3. customto remove the solvent
  4. additionThe residue was added with xylene (20 ml)
  5. stirringby stirring at 160° C. for 3 days
  6. temperatureAfter the reaction mixture was cooled to room temperature
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe extract was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationdistilled under reduced pressure
  11. customto remove the solvent
  12. customto collect chloroform/ethyl acetate (10/1) eluate fractions
  13. custompurified by chromatography

Sources & evidence

ORD record
ord-be936a977f214690a5c8aef2330c4e5b
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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