Dichloromethane → HCID 57837481, compound

HRID 731738Notes

Reaction equation

HRID 731738 reaction equation
I[C:2]1[C:3]([CH:11]([CH3:13])[CH3:12])=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.O.[NH2:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.ClCCl.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[CH:11]([C:3]1[C:2]([C:20]2[CH:21]=[C:16]([NH2:15])[CH:17]=[CH:18][CH:19]=2)=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 143894233-Aminophenylboronic acid monohydrateHCID 57837525HCID 57837525, compound

Product 1

HCID 57837481HCID 57837481, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 20 ml microwave reaction vial was added 3-iodo-2-isopropyl-pyrazolo[1,5-a]pyridine (690 mg, 2.41 mmol), 3-aminophenylboronic acid monohydrate (411 mg, 2.65 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (197 mg, 0.24 mmol), acetonitrile (8 ml), and 1 M aqueous Na2CO3 solution (5 ml). The mixture was placed in a microwave reactor for 2 hours at 140° C. The reaction mixture was concentrated in vacuo, and the crude material partitioned between dichloromethane and water. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by silica gel flash chromatography (0 to 30% ethyl acetate in hexanes) to give 205 mg (34%) of 3-(2-isopropyl-pyrazolo[1,5-a]pyridin-3-yl)-phenylamine. 1H-NMR (250 MHz, DMSO-d6) δ 8.40 (d, J=7.0 Hz, 1H), 7.44 (d, J=9.0 Hz, 1H), 7.25-7.18 (m, 1H), 7.03-6.97 (m, 1H), 6.81 (d, J=7.3 Hz, 1H), 6.71 (s, 1H), 6.67-6.62 (m, 2H), 3.65 (broad s, 2H), 3.35 (sept, J=6.9 Hz, 1H), 1.35 (d, J=6.8 Hz, 6H). LC/MS 252.3 m/z (M+H+). Compound 1100.

Workup

  1. customTo a 20 ml microwave reaction
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe crude material partitioned between dichloromethane and water
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by silica gel flash chromatography (0 to 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-67139b3a94f94477937f4ed21a83ad64
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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