Acetone → HCID 86638476, compound

HRID 1662006Notes

Reaction equation

HRID 1662006 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1C(O)=O)[N:10]([CH3:17])[N:9]=[CH:8]2.C1(P([N:39]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C[C:43](C)=[O:44].[C:46]([OH:50])([CH3:49])([CH3:48])[CH3:47]>>[F:1][C:2]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[NH:39][C:43](=[O:44])[O:50][C:46]([CH3:49])([CH3:48])[CH3:47])[N:10]([CH3:17])[N:9]=[CH:8]2

Participants

5

Reactant 4

HCID 180AcetoneHCID 6386tert-ButanolHCID 199401P,P-Diphenylphosphinic azideHCID 66766818HCID 66766818, compound

Product 1

HCID 86638476HCID 86638476, compoundYield 47.9%

Procedure

The suspension of 5-(2-fluoro-4-nitrophenoxy)-1-methyl-1H-indazole-6-carboxylic acid (1.1 g, 3.3 mmol), diphenyl phosphoryl azide (0.91 g, 3.3 mmol), TEA (0.33 g, 3.3 mmol) and 4 Å molecular sieve (2.5 g) in tert-butanol (50 mL) is heated at reflux overnight. Then the solid is filtered off and the filtrate is concentrated. The residue is partitioned between saturated aqueous sodium chloride (40 mL) and EtOAc (100 mL). The organic phase is separated, dried and concentrated and the residue is purified by silica gel column chromatography eluting with PE:acetone (4:1) to give the product (0.64 g, 47.9% yield). MS (m/z): 403.1 (M+H).

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. filtrationThen the solid is filtered off
  4. concentrationthe filtrate is concentrated
  5. customThe residue is partitioned between saturated aqueous sodium chloride (40 mL) and EtOAc (100 mL)
  6. customThe organic phase is separated
  7. customdried
  8. concentrationconcentrated
  9. customthe residue is purified by silica gel column chromatography
  10. washeluting with PE

Sources & evidence

ORD record
ord-6453e4750d2a4fdc8c8c45184beb5787
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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