(Diethylamino)sulfur trifluoride → 1-(6-(4-fluoroazepan-4-yl)pyridin-2-yl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 57952Notes

Reaction equation

HRID 57952 reaction equation
O[C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]3[C:30]4[CH:29]=[C:28]([C:31]5[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=5)[N:27]=[CH:26][C:25]=4[CH:24]=[N:23]3)[N:17]=2)[CH2:8][CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.C(N(S(F)(F)[F:43])CC)C>C(Cl)Cl>[F:43][C:2]1([C:16]2[N:17]=[C:18]([N:22]3[C:30]4[CH:29]=[C:28]([C:31]5[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=5)[N:27]=[CH:26][C:25]=4[CH:24]=[N:23]3)[CH:19]=[CH:20][CH:21]=2)[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 86707129tert-butyl 4-hydroxy-4-(6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)azepane-1-carboxylate

Product 1

HCID 867071371-(6-(4-fluoroazepan-4-yl)pyridin-2-yl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridineYield 110.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-hydroxy-4-(6-(6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)azepane-1-carboxylate (150 mg, 0.3 mmol) in DCM (5 mL) was added diethylaminosulfur trifluoride (DAST, 0.12 mL, 0.9 mmol). The mixture was stirred at room temperature for 1 hour, which was monitored by LCMS. After completion of the reaction, it was concentrated under reduced pressure to afford 1-(6-(4-fluoroazepan-4-yl)pyridin-2-yl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridine as a light yellow oil (130 mg, 87%). MS (ESI) m/z: 493 [M+H]+.

Workup

  1. customAfter completion of the reaction, it
  2. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-fbd6e3303a944a2290779bfb7ce2c7b4
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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