Indoline → HCID 58778530, compound

HRID 1372771Notes

Reaction equation

HRID 1372771 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH:10]1N=CN(C(N2C=NC=C2)=S)C=1.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:32][CH3:33])=[O:31])=[C:25]([F:34])[C:24]=1[OH:35]>C1COCC1>[F:34][C:25]1[C:24]2[O:35][C:10]([N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]3)=[N:22][C:23]=2[CH:28]=[CH:27][C:26]=1[CH2:29][C:30]([O:32][CH3:33])=[O:31]

Participants

5

Reactant 3

HCID 10328IndolineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 17859032Methyl (4-amino-2-fluoro-3-hydroxyphenyl)acetate

Product 1

HCID 58778530HCID 58778530, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Indoline (0.49 ml, 4.36 mmol) was dissolved in THF (20 ml). To the resulting solution was added N,N′-thiocarbonyldiimidazole (863 mg, 4.36 mmol). The resulting mixture was stirred at room temperature for 14 hours. Methyl 4-amino-2-fluoro-3-hydroxyphenylacetate (1.0 g, 5.0 mmol) was added to the reaction mixture, followed by stirring at 70° C. for 1 day. Mercuric oxide (yellow) (944 mg, 4.36 mmol) was added to the reaction mixture and the resulting mixture was heated at 70° C. for 15 hours. After cooling to room temperature, the reaction mixture was filtered through Celite, followed by washing with methanol. The filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform/ethyl acetate (10/1) eluate fractions, methyl (7-fluoro-2-(1-indolinyl)-6-benzoxazolyl)acetate (330 mg, 23%) was obtained as a pale brown solid.

Workup

  1. stirringby stirring at 70° C. for 1 day
  2. temperaturethe resulting mixture was heated at 70° C. for 15 hours
  3. temperatureAfter cooling to room temperature
  4. filtrationthe reaction mixture was filtered through Celite
  5. washby washing with methanol
  6. distillationThe filtrate was distilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column, whereby from chloroform/ethyl acetate (10/1) eluate fractions

Sources & evidence

ORD record
ord-a2245d8a2d4c4fb29fe11695b24a57c0
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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