Methyl 2-azidoacetate → 6-Benzyloxy-5-fluoro-1H-indole-2-carboxylic acid methyl ester

HRID 901095

Reaction equation

HRID 901095 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH3:8])=[O:6])=[N+]=[N-].[CH2:9]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][C:18]=1[F:25])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:8][O:7][C:5]([C:4]1[NH:1][C:23]2[C:20]([CH:21]=1)=[CH:19][C:18]([F:25])=[C:17]([O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:24]=2)=[O:6]

Participants

5

Reactant 3

HCID 4020482Methyl 2-azidoacetateHCID 10942334Sodium MethoxideHCID 219768984-(Benzyloxy)-3-fluorobenzaldehyde

Product 1

HCID 441851846-Benzyloxy-5-fluoro-1H-indole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 2-azidoacetate, 4-benzyloxy-3-fluoro-benzaldehyde and sodium methanolate (in methanol) in toluene was reacted for 3 h at 0° C. The residue after filtration of the suspension was washed with methanol, partitioned between ethyl acetate and ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were dried with Na2SO4, evaporated to dryness and the residue taken up in p-xylene and brought to reflux temperature for 2 h. After concentration the mixture was left to crystallize and the formed crystals were filtered off and washed with toluene. The title compound was after drying at 40° C. under vacuum obtained as yellow crystals. MS (m/e): 300.3 (MH+, 100%).

Workup

  1. customwas reacted for 3 h at 0° C
  2. filtrationThe residue after filtration of the suspension
  3. washwas washed with methanol
  4. custompartitioned between ethyl acetate and ammonium chloride solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried with Na2SO4
  7. customevaporated to dryness
  8. temperatureto reflux temperature for 2 h
  9. concentrationAfter concentration the mixture
  10. waitwas left
  11. customto crystallize
  12. filtrationthe formed crystals were filtered off
  13. washwashed with toluene
  14. customafter drying at 40° C. under vacuum
  15. customobtained as yellow crystals

Sources & evidence

ORD record
ord-c7211191e30344998a917845c1ebeb64
Source dataset
uspto-grants-2008_04
Patent number
US07361682B2

Linked notes

Loading…