Acetonitrile → HCID 57731440, compound

HRID 2234695Notes

Reaction equation

HRID 2234695 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=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]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[CH:10]=1.Br[C:38]1[CH:39]=[CH:40][C:41]([NH:49][C:50]2[CH:51]=[N:52][CH:53]=[N:54][CH:55]=2)=[C:42]([CH:48]=1)[C:43]([N:45]([CH3:47])[CH3:46])=[O:44].C(#N)C.C(=O)(O)[O-].[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].O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:38]3[CH:39]=[CH:40][C:41]([NH:49][C:50]4[CH:51]=[N:52][CH:53]=[N:54][CH:55]=4)=[C:42]([CH:48]=3)[C:43]([N:45]([CH3:47])[CH3:46])=[O:44])[CH:16]=2)[N:11]([S:27]([C:30]2[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=2)(=[O:29])=[O:28])[CH:10]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 160390673-(2-Methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 57731560HCID 57731560, compound

Product 1

HCID 57731440HCID 57731440, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 8028TetrahydrofuranSolvent

Procedure

125 mg (0.25 mmol) of 3-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine, 14 mg (17 μmol) of dichloro[1,1′-bis(diphenylphoshino)ferrocene]palladium(II) dichloromethane adduct and 65 mg (0.22 mmol) of 5-bromo-N,N-dimethyl-2-(pyrimidin-5-ylamino)-benzamide were place in a microwave vial. 1.5 mL of acetonitrile, 0.75 mL of tetrahydrofuran and 1.5 mL of a saturated aqueous solution of sodium bicarbonate were added. The vial was sealed and irradiated in a Personal Chemistry® Optimizer to 130° C. for 20 min. The organic layer was separated and evaporated. The resulting residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate containing 10% v/v of methanol in hexanes to afford 67 mg (0.11 mmol, 50%) of 5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-(pyrimidin-5-ylamino)-benzamide. MS: m/z 619.0 (M+H+).

Workup

  1. customThe vial was sealed
  2. customirradiated in a Personal Chemistry® Optimizer to 130° C. for 20 min
  3. customThe organic layer was separated
  4. customevaporated
  5. customThe resulting residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate containing 10% v/v of methanol in hexanes

Sources & evidence

ORD record
ord-a12c0fc8c97149f783100082a36c856c
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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