Water → tert-butyl 4-[4-(1-hydroxy-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

HRID 1404596Notes

Reaction equation

HRID 1404596 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][N:14]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[CH:15]=2)=[CH:7][C:6]=1[N+:29]([O-])=[O:30].O.O.Cl[Sn]Cl.O>CCOC(C)=O>[OH:30][N:29]1[C:6]2[C:5](=[N:10][CH:9]=[C:8]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:18][CH2:17]4)[CH:15]=3)[CH:7]=2)[CH:4]=[CH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 58532279tert-butyl 4-(4-{6-[(E)-2-(dimethylamino)ethenyl]-5-nitropyridin-3-yl}-1H-pyrazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 67458749tert-butyl 4-[4-(1-hydroxy-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

tert-butyl 4-(4-{6-[(E)-2-(dimethylamino)ethenyl]-5-nitropyridin-3-yl}-1H-pyrazol-1-yl)piperidine-1-carboxylate (366 mg, 0.81 mmol) and SnCl2.2H2O (966 mg, 4.26 mmol, 5.0 eq) in 3 ml of EtOAc were stirred at r.t. for 2 hours. EtOAc and water were added and layers were separated. The aqueous layer was extracted with EtOAc, washed with sat. NH4Cl and brine. After evaporation, the crude product was chromatographed (Mesh/DCM 1:20) to give a yellow solid, 170 mg, in 54% yield.

Workup

  1. customlayers were separated
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washwashed with sat. NH4Cl and brine
  4. customAfter evaporation
  5. customthe crude product was chromatographed (Mesh/DCM 1:20)
  6. customto give a yellow solid, 170 mg

Sources & evidence

ORD record
ord-7f18c60015f3474590a97fae95dc1738
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

Loading…