Triethylamine → tert-butyl 6-bromo-1H-pyrazolo[4,3-b]pyridine-1-carboxylate

HRID 2284564Notes

Reaction equation

HRID 2284564 reaction equation
BrC1C=[C:4]2[CH:10]=[N:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:5]2=NC=1.[Br:18][C:19]1[CH:20]=C2NN=CC2=[N:23][CH:24]=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.CCN(CC)CC>CN(C)C1C=CN=CC=1.C(#N)C>[Br:18][C:19]1[CH:20]=[C:5]2[N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[N:9]=[CH:10][C:4]2=[N:23][CH:24]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 401522596-Bromo-1H-pyrazolo[4,3-b]pyridineHCID 50986454tert-Butyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate2×

Product 1

HCID 86715472tert-butyl 6-bromo-1H-pyrazolo[4,3-b]pyridine-1-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

Analogous to the preparation of tert-butyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate, 6-bromo-1H-pyrazolo[4,3-b]pyridine (2.0 g, 10.10 mmol) was reacted with di-tert-butyl dicarbonate (2.8 g, 13.10 mmol), NEt3 (1.44 g, 2.0 mL, 14 mmol) and 4-(dimethylamino)pyridine in acetonitrile (20 mL) for 3 h. Work-up as discussed previously in the preparation of tert-butyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate provided desired product of tert-butyl 6-bromo-1H-pyrazolo[4,3-b]pyridine-1-carboxylate as a brown solid (2.8 g, 93%).

Sources & evidence

ORD record
ord-5aab59fe29124a0b8ad8dbb22356177a
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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