Water → 3-(1-Isopropyltriazol-4-yl)-5-(1-methylindol-5-yl)pyridin-2-amine

HRID 632484Notes

Reaction equation

HRID 632484 reaction equation
Br[C:2]1[CH: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.[K+].[K+]>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)[CH:3]=2)[N:10]=[N:11]1)([CH3:16])[CH3:15]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27598671-Methyl-1H-indole-5-boronic acidHCID 902731555-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyridin-2-ylamine

Product 1

HCID 771059603-(1-Isopropyltriazol-4-yl)-5-(1-methylindol-5-yl)pyridin-2-amine

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)-pyridin-2-ylamine (200 mg, 0.708 mmol) and N-methylindole-5-boronic acid (124 mg, 0.708 mmol) in 1,4-dioxane (6.0 mL)/water (3.0 mL) was added K2CO3 (293 mg, 2.126 mmol) at room temperature. The reaction mixture was purged with argon for 30 min. Then Pd(PPh3)4 (41 mg, 0.035 mmol) was added and the mixture was 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 compound. Crude compound was purified by column using 100-200 mesh silica gel. The column was eluted with 80% EtOAc in Pet. Ether to afford the title compound as pale 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 compound
  8. customCrude compound was purified by column
  9. washThe column was eluted with 80% EtOAc in Pet. Ether

Sources & evidence

ORD record
ord-fca56486c17945228f859e062c0b972a
Source dataset
uspto-grants-2016_04
Patent number
US09321748B2

Reaction notes

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