Water → HCID 90273484, compound

HRID 1053113Notes

Reaction equation

HRID 1053113 reaction equation
Br[C:2]1[N:3]=[C:4]([C:9]2[N:10]=[N:11][N:12]([CH:14]([CH3:16])[CH3:15])[CH:13]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:17][N:18]1[C:26]2[C:21](=[CH:22][C:23](B(O)O)=[CH:24][CH:25]=2)[CH:20]=[CH:19]1.O.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:14]([N:12]1[CH:13]=[C:9]([C:4]2[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:23]3[CH:22]=[C:21]4[C:26](=[CH:25][CH:24]=3)[N:18]([CH3:17])[CH:19]=[CH:20]4)[N:3]=2)[N:10]=[N:11]1)([CH3:16])[CH3:15]

Participants

8

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27598671-Methyl-1H-indole-5-boronic acidHCID 90273228HCID 90273228, compound

Product 1

HCID 90273484HCID 90273484, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyrazin-2-ylamine (750 mg, 2.65 mmol) and N-methylindole-5-boronic acid (556 mg, 3.18 mmol) in 1,4-dioxane (15.0 mL)/water (5.0 mL) was added Cs2CO3 (1.29 g, 3.97 mmol) at room temperature. The reaction mixture was purged with argon for 30 min. Then Pd(PPh3)4 (153 mg, 0.13 mmol) was added and allowed to stir at 100° C. for 16 h. The reaction mixture was cooled to RT, diluted with EtOAc (20 mL) and washed with water (20 mL). The organic layer was washed with brine solution (20 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure to afford crude product. The crude compound was purified by column using 100-200 mesh silica gel. The column was eluted with 70-80% EtOAc in Hexane to afford the title compound as a yellow solid.

Workup

  1. customThe reaction mixture was purged with argon for 30 min
  2. temperatureThe reaction mixture was cooled to RT
  3. washwashed with water (20 mL)
  4. washThe organic layer was washed with brine solution (20 mL)
  5. dry with materialdried over anhydrous Na2SO4 and solvent
  6. customwas evaporated under reduced pressure
  7. customto afford crude product
  8. customThe crude compound was purified by column
  9. washThe column was eluted with 70-80% EtOAc in Hexane

Sources & evidence

ORD record
ord-6cc356970c8646b5804078c290307b59
Source dataset
uspto-grants-2016_07
Patent number
US09393248B1

Reaction notes

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