Dichloromethane → HCID 77106759, compound

HRID 1053130Notes

Reaction equation

HRID 1053130 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.CC1(C)C(C)(C)OB([C:25]2[CH:37]=[CH:36][C:28]([CH2:29][N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[CH:27][CH:26]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+].C(Cl)Cl>COCCOC.CCOC(C)=O.O>[CH:14]([N:12]1[CH:13]=[C:9]([C:4]2[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:25]3[CH:26]=[CH:27][C:28]([CH2:29][N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[CH:36][CH:37]=3)[CH:3]=2)[N:10]=[N:11]1)([CH3:16])[CH3:15]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27955024-((Morpholino)methyl)phenylboronic acid pinacol esterHCID 902731555-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyridin-2-ylamine

Product 1

HCID 77106759HCID 77106759, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 5-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyridin-2-ylamine (500 mg, 1.77 mmol) and 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-morpholine (537 mg, 1.77 mmol) in ethylene glycol dimethyl ether (6.0 mL)/water (4.0 mL) was added Cs2CO3 (1.15 g, 3.54 mmol) at room temperature. The reaction mixture was purged with argon for 30 min. Then Pd(dppf)Cl2.DCM (72.2 mg, 0.08 mmol) was added and allowed to stir at 140° C. for 6 h in microwave. After 6 h, the reaction mixture was cooled to RT, diluted with EtOAc (50 mL) and washed with water (50 mL). The organic layer was washed with brine solution (50 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 5-95% MeOH in DCM to afford the title compound as a brown solid.

Workup

  1. customThe reaction mixture was purged with argon for 30 min
  2. waitAfter 6 h
  3. temperaturethe reaction mixture was cooled to RT
  4. washwashed with water (50 mL)
  5. washThe organic layer was washed with brine solution (50 mL)
  6. dry with materialdried over anhydrous Na2SO4 and solvent
  7. customwas evaporated under reduced pressure
  8. customto afford crude product
  9. customThe crude compound was purified by column
  10. washThe column was eluted with 5-95% MeOH in DCM

Sources & evidence

ORD record
ord-c6263e1adefe496c8bc0ca2b02fcf0d5
Source dataset
uspto-grants-2016_07
Patent number
US09393248B1

Reaction notes

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