Cesium carbonate → HCID 58407640, compound

HRID 1521776Notes

Reaction equation

HRID 1521776 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=[C:9]2I.[C:24](=O)([O-])[O-:25].[Cs+].[Cs+].CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C>CO.[Cu]I>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=[C:9]2[O:25][CH3:24]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 584076045-(1,3-Dioxolan-2-yl)-3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

Product 1

HCID 58407640HCID 58407640, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

To a microwave-flask containing 300 mg (0.672 mmol) 5-(1,3-dioxolan-2-yl)-3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole (Example 5A), 438 mg (1.344 mmol) cesium carbonate and 32 mg (0.134 mmol) 3,4,7,8-tetramethyl-1,10-phenanthroline in methanol (4 ml) were added 13 mg (0.067 mmol) copper(I) iodide. The flask was placed in an ultrasonic bath, and argon was bubbled through for a period of five minutes. The flask was then sealed and heated to 140° C. for 2 h using microwave irradiation. The reaction mixture was filtered over celite which was washed with acetonitrile. The filtrates of a total of seven reactions at this scale were combined and purified by preparative RP-HPLC (acetonitrile/water gradient) to afford 940 mg (57% of th.) of the title compound.

Workup

  1. customThe flask was placed in an ultrasonic bath
  2. customargon was bubbled through for a period of five minutes
  3. customThe flask was then sealed
  4. custommicrowave irradiation
  5. filtrationThe reaction mixture was filtered over celite which
  6. washwas washed with acetonitrile
  7. custompurified by preparative RP-HPLC (acetonitrile/water gradient)

Sources & evidence

ORD record
ord-0b21608617824746bbd563a0bc532961
Source dataset
uspto-grants-2015_07
Patent number
US09073939B2

Reaction notes

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