Potassium Carbonate → 6-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1-{[2-(trifluoromethyl)benzyl]oxy}-1H-pyrrolo[3,2-b]pyridine

HRID 1404597Notes

Reaction equation

HRID 1404597 reaction equation
[OH:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]4)[CH:15]=3)[CH:9]=2)[CH:4]=[CH:3]1.Br[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]([F:40])([F:39])[F:38].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH:19]1[CH2:20][CH2:21][CH:16]([N:14]2[CH:15]=[C:11]([C:8]3[CH:9]=[C:10]4[N:2]([O:1][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=5[C:37]([F:40])([F:39])[F:38])[CH:3]=[CH:4][C:5]4=[N:6][CH:7]=3)[CH:12]=[N:13]2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 67458749tert-butyl 4-[4-(1-hydroxy-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Product 1

HCID 462350476-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1-{[2-(trifluoromethyl)benzyl]oxy}-1H-pyrrolo[3,2-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-butyl 4-[4-(1-hydroxy-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate (30 mg, 0.078 mmol, 1.0 eq), 1-(bromomethyl)-2-(trifluoromethyl)benzene (0.066 mmol), and K2CO3 (30 mg) in 1.5 ml of DMF were shaken at r.t. for 30 min and then filtered and evaporated. The resulting crude product was dissolved in 1.5 ml of methanol and 0.5 ml of 4.0 M HCl/dioxane was dropped in. The reaction was shaken at room temperature for 0.5-1 h. The solvent was evaporated and the residue was dissolved in 2 ml of DCM. To this solution were added 20 mg of NaHCO3, 10 mg of Na2CO3, and drops of water. After stirred for 10 min, the organic solution was separated and purified with preparation HPLC to give the final product.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. dissolutionThe resulting crude product was dissolved in 1.5 ml of methanol
  4. addition0.5 ml of 4.0 M HCl/dioxane was dropped in
  5. customThe solvent was evaporated
  6. dissolutionthe residue was dissolved in 2 ml of DCM
  7. additionTo this solution were added 20 mg of NaHCO3, 10 mg of Na2CO3, and drops of water
  8. stirringAfter stirred for 10 min
  9. customthe organic solution was separated
  10. custompurified with preparation HPLC

Sources & evidence

ORD record
ord-7cf10928087e43148d2e0db5591870eb
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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