Tetrahydrofuran → HCID 68663647, compound

HRID 1865664Notes

Reaction equation

HRID 1865664 reaction equation
COC1C=CC=CC=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15](B3OC(C)(C)C(C)(C)O3)[CH:16]=2)[N:11]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[N:10]=1.[NH2:35][C:36]1[CH:46]=[CH:45][C:44](I)=[CH:43][C:37]=1[C:38]([N:40]([CH3:42])[CH3:41])=[O:39].C1COCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].C(#N)C>[NH2:35][C:36]1[CH:46]=[CH:45][C:44]([C:15]2[CH:16]=[C:17]3[CH:9]=[N:10][N:11]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:33])[CH3:34])[C:12]3=[N:13][CH:14]=2)=[CH:43][C:37]=1[C:38]([N:40]([CH3:42])[CH3:41])=[O:39]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 40049759HCID 40049759, compoundHCID 598360923-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxy-methyl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 68663647HCID 68663647, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine (1.0 g, 2.1 mmol) and 2-amino-5-iodo-N,N-dimethylbenzamide (0.67 g, 2.3 mmol) in a 20 mL microwave reaction flask was added THF (6 mL), acetonitrile (6 mL), and 1 N aqueous sodium carbonate (6 mL, 6 mmol). The resulting suspension was degassed with nitrogen for 2 minutes. dichloro[1,1′-bis(diphenylphoshino)ferrocene]palladium(II) dichloromethane adduct (106 mg, 0.13 mmol) was added and degas was continued for another minute. The flask was capped and irradiated in a microwave reactor to 150° C. for 30 min. The reaction mixture was partitioned between aqueous saturated sodium chloride and ethyl acetate (50 mL:50 mL). The aqueous layers were extracted with ethyl acetate (30 mL×3). The combined organic phases were washed with brine, dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel with a gradient of ethyl acetate in hexane to afford 2-amino-N,N-dimethyl-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzamide as a pale yellow solid (55%). MS: m/z 518 (M+H+).

Workup

  1. customin a 20 mL microwave reaction flask
  2. customThe resulting suspension was degassed with nitrogen for 2 minutes
  3. customdegas
  4. customThe flask was capped
  5. customirradiated in a microwave reactor to 150° C. for 30 min
  6. customThe reaction mixture was partitioned between aqueous saturated sodium chloride and ethyl acetate (50 mL:50 mL)
  7. extractionThe aqueous layers were extracted with ethyl acetate (30 mL×3)
  8. washThe combined organic phases were washed with brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. customThe resulting crude was purified by flash chromatography on silica gel with a gradient of ethyl acetate in hexane

Sources & evidence

ORD record
ord-13fe51be37eb4146b99b80c2626d2b85
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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