Triethylamine → 1-Boc-3-methyl-6-fluoro-1H-pyrazolo[3,4-B]pyridine

HRID 1157410Notes

Reaction equation

HRID 1157410 reaction equation
[F:1][C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([CH3:11])[C:5]2=[CH:4][CH:3]=1.C(N(CC)CC)C.[O:19](C(OC(C)(C)C)=O)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=O>C(#N)C.CN(C1C=CN=CC=1)C>[F:1][C:2]1[N:7]=[C:6]2[N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:19])[N:9]=[C:10]([CH3:11])[C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 178434471HCID 178434471, compound

Product 1

HCID 251322461-Boc-3-methyl-6-fluoro-1H-pyrazolo[3,4-B]pyridine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×

Procedure

A stirred solution of 6.67 g (44.2 mmol) of 6-fluoro-3-methyl-1H-pyrazolo[3,4-b]pyridine in 100 mL of acetonitrile under nitrogen was treated with 5.40 g (44.2 mmol) of DMAP and 6.46 mL (46.4 mmol) of triethylamine. A solution of 11.56 g (53.0 mmol) of (BOC)2O in 20 mL acetonitrile was added dropwise via a cannula and the resulting reaction mixture stirred for 1 hour until completion as determined by LC/MS analysis. The reaction was quenched with brine and extracted with EtOAc (3×). The combined organic layers were washed with H2O, brine, dried over MgSO4, and concentrated in vacuo. The crude material was purified via silica gel chromatography (0-70% EtOAc/hexane) to yield the title compound. 1H NMR (CDCl3): 1.74 (s, 9H), 2.60 (s, 3H), 6.95 (d, 1H), 8.08 (t, 1H).

Workup

  1. customthe resulting reaction mixture
  2. customThe reaction was quenched with brine
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organic layers were washed with H2O, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified via silica gel chromatography (0-70% EtOAc/hexane)

Sources & evidence

ORD record
ord-b34cbefeb910422ba20cf3485c85a3f5
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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