Potassium Carbonate → HCID 118078991, compound

HRID 1485779Notes

Reaction equation

HRID 1485779 reaction equation
Br[C:2]1[CH:22]=[N:21][C:5]2[N:6]([C:17](=[O:20])[NH:18][CH3:19])[C@@H:7]([CH3:16])[CH2:8][N:9]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[C:4]=2[CH:3]=1.[CH:23]1([N:26]2[CH:30]=[C:29](B3OC(C)(C)C(C)(C)O3)[CH:28]=[N:27]2)[CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>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].ClCCl>[CH:23]1([N:26]2[CH:30]=[C:29]([C:2]3[CH:22]=[N:21][C:5]4[N:6]([C:17](=[O:20])[NH:18][CH3:19])[C@@H:7]([CH3:16])[CH2:8][N:9]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[C:4]=4[CH:3]=3)[CH:28]=[N:27]2)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 593271331-Cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 118079349HCID 118079349, compound

Product 1

HCID 118078991HCID 118078991, compound

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A reaction vial was charged with (S)-isopropyl 7-bromo-3-methyl-4-(methylcarbamoyl)-3,4-dihydropyrido[2,3-b]pyrazine-1 (2H)-carboxylate (0.015 g, 0.04 mmol), 1-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.2 M solution in 1,4-dioxane, 0.40 mL, 0.080 mmol), potassium carbonate (1.0 M solution in water, 0.120 mL, 0.120 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.02 M solution in 1,2-dichloroethane, 0.200 mL, 0.004 mmol). The reaction was purged with nitrogen and heated to 80° C. on a heater shaker overnight. The reaction was diluted with ethyl acetate and washed with brine. The combined organic layers were concentrated under a stream of nitrogen. The crude product was purified by mass triggered preparatory HPLC. The product-containing fractions were combined and concentrated to afford (S)-isopropyl 7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-4-(methylcarbamoyl)-3,4-dihydropyrido[2,3-b]pyrazine-1(2H)-carboxylate. MS (ESI, pos. ion) m/z 399 [M+H]+.

Workup

  1. customA reaction
  2. customThe reaction was purged with nitrogen
  3. additionThe reaction was diluted with ethyl acetate
  4. washwashed with brine
  5. concentrationThe combined organic layers were concentrated under a stream of nitrogen
  6. customThe crude product was purified by mass
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3e2b59dfd16840a08ff95954c179814e
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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