1-Amino-5-chloro-2-(prop-1-yn-1-yl)-3-((2-(trimethylsilyl)ethoxy)methoxy)pyridin-1-ium 2,4,6-trimethylbenzenesulfonate → 6-Chloro-2-methylpyrazolo[1,5-a]pyridin-4-ol

HRID 2209260Notes

Reaction equation

HRID 2209260 reaction equation
CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([O:22]COCC[Si](C)(C)C)[C:16]=1[C:31]#[C:32][CH3:33]>CC(O)=O>[Cl:21][C:19]1[CH:18]=[C:17]([OH:22])[C:16]2[N:15]([N:14]=[C:32]([CH3:33])[CH:31]=2)[CH:20]=1

Participants

3

Reactant 1

HCID 1317359841-Amino-5-chloro-2-(prop-1-yn-1-yl)-3-((2-(trimethylsilyl)ethoxy)methoxy)pyridin-1-ium 2,4,6-trimethylbenzenesulfonate

Product 1

HCID 1178440256-Chloro-2-methylpyrazolo[1,5-a]pyridin-4-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

AcOH (5 mL) was added to 1-amino-5-chloro-2-(prop-1-yn-1-yl)-3-((2-(trimethylsilyl)ethoxy)methoxy)pyridin-1-ium 2,4,6-trimethylbenzenesulfonate. After stirring overnight, the AcOH was removed under vaco., the residue was treated with 2 M solution of LiOH (5 mL) at rt., and extracted with ethyl acetate. Combined organics were washed with brine, dried, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to provide of 6-chloro-2-methylpyrazolo[1,5-a]pyridin-4-ol 6.59. LCMS [M+H]+: 183.09. 1H NMR (400 MHz, CDCl3) ppm: δ 8.028 (s, 1H), 6.419 (d, J=6.8 Hz, 1H), 6.398 (d, J=6.8 Hz, 1H), 2.395 (s, 3H).

Workup

  1. customthe AcOH was removed under vaco
  2. addition, the residue was treated with 2 M solution of LiOH (5 mL) at rt
  3. extraction, and extracted with ethyl acetate
  4. washCombined organics were washed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b5188f07eb0c4027aa68a9a6f726d3d3
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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