Triethylamine → Tert-butyl 3-methyl-1H-pyrazolo[3,4-B]pyridine-1-carboxylate

HRID 1157407Notes

Reaction equation

HRID 1157407 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.C(N(CC)CC)C.[O:18](C(OC(C)(C)C)=O)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=O>C(#N)C.CN(C1C=CN=CC=1)C>[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])[N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 178434440HCID 178434440, compound

Product 1

HCID 57370583Tert-butyl 3-methyl-1H-pyrazolo[3,4-B]pyridine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×

Procedure

A stirred solution of 692 mg (5.20 mmol) of 3-methyl-1H-pyrazolo[3,4-b]pyridine in 25 mL of acetonitrile under nitrogen was cooled to 0° C. in an ice bath, and was treated with 635 mg (5.20 mmol) of DMAP and 761 μL (5.46 mmol) of triethylamine. A solution of 1.36 g (6.24 mmol) of (BOC)2O in 5 mL acetonitrile was then added dropwise using an addition funnel. Upon completion of addition, the ice bath was removed and the mixture was stirred for an additional 18 hours at room temperature. Solvent was removed in vacuo, and the residue was partitioned between EtOAc and H2O. The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo to an orange oil. This crude material was purified by flash chromatography over silica gel with 1:1 ethyl acetate/hexanes to give the title product as a clear oil. 1H NMR (CDCl3): 1.74 (s, 9H), 2.60 (s, 3H), 7.29 (m, 1H), 8.02 (dd, 1H), 8.74 (dd, 1H).

Workup

  1. additionUpon completion of addition
  2. customthe ice bath was removed
  3. customSolvent was removed in vacuo
  4. customthe residue was partitioned between EtOAc and H2O
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to an orange oil
  9. customThis crude material was purified by flash chromatography over silica gel with 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-174ae3ceabe747b19738d76244418df2
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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