Potassium Carbonate → tert-Butyl ((1S)-1-(6-(3,5-dimethyl-1H-pyrazol-4-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate

HRID 75295Notes

Reaction equation

HRID 75295 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:20]([CH3:21])[CH:19]=[CH:18][C:5]2=[N:6][C:7]=1[C@@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9].[CH3:22][C:23]1[C:27](B2OC(C)(C)C(C)(C)O2)=[C:26]([CH3:37])[NH:25][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:22][C:23]1[C:27]([C:2]2[CH:3]=[C:4]3[N:20]([CH3:21])[CH:19]=[CH:18][C:5]3=[N:6][C:7]=2[C@@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[C:26]([CH3:37])[NH:25][N:24]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 162177133,5-Dimethylpyrazole-4-boronic acid, pinacol esterHCID 86707985(S)-tert-butyl (1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate

Product 1

HCID 86707984tert-Butyl ((1S)-1-(6-(3,5-dimethyl-1H-pyrazol-4-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (S)-tert-butyl (1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate (2 g, 5.65 mmol), 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1160 mg, 5.20 mmol) and PdCl2(dppf)-CH2Cl2 adduct (147 mg, 0.180 mmol) in dioxane (3500 μL) and aqueous 3M potassium carbonate solution (5400 μL, 16 mmol) was heated at 120° C. for 5 hours in a microwave reactor. The mixture was diluted with ethyl acetate (177 mL), washed with saturated ammonium chloride (177 mL) and brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified on silica gel, eluting with EtOAc to give the title compound. ESI-MS m/z [M+H]+ calc'd for C20H27N5O2, 370.2. found 370.6.

Workup

  1. washwashed with saturated ammonium chloride (177 mL) and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified on silica gel
  5. washeluting with EtOAc

Sources & evidence

ORD record
ord-d9647670216f48fcab00254d6b6068ff
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

Loading…