Potassium Carbonate → 1-tert-Butyl-5-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(5-methoxy-2-pyrazol-1-yl-phenyl)-1H-benzimidazole

HRID 1966700Notes

Reaction equation

HRID 1966700 reaction equation
[C:1]([N:5]1[C:9]2[CH:10]=[CH:11][C:12](B3OC(C)(C)C(C)(C)O3)=[CH:13][C:8]=2[N:7]=[C:6]1[C:23]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:24]=1[N:31]1[CH:35]=[CH:34][CH:33]=[N:32]1)([CH3:4])([CH3:3])[CH3:2].Br[C:37]1[CH:38]=[C:39]2[CH2:45][CH2:44][NH:43][C:40]2=[N:41][CH:42]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[C:1]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:37]3[CH:38]=[C:39]4[CH2:45][CH2:44][NH:43][C:40]4=[N:41][CH:42]=3)=[CH:13][C:8]=2[N:7]=[C:6]1[C:23]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:24]=1[N:31]1[CH:35]=[CH:34][CH:33]=[N:32]1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 219640795-Bromo-2,3-dihydro-7-azaindoleHCID 585420761-tert-butyl-2-(5-methoxy-2-pyrazol-1-yl-phenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole

Product 1

HCID 532392081-tert-Butyl-5-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(5-methoxy-2-pyrazol-1-yl-phenyl)-1H-benzimidazoleYield 17.2%

Reagents, catalysts & solvents 3

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)CatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In a microwave vial are combined 1-tert-butyl-2-(5-methoxy-2-pyrazol-1-yl-phenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole (285 mg, 0.60 mmol), 5-bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.50 mmol), potassium carbonate (140 mg, 1.0 mmol), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (53 mg, 0.08 mmol) in toluene (3.0 mL) and water (0.30 mL). The reaction vial is sealed and stirred at 100° C. for 4 hours in an oil bath. After this time the reaction is cooled and poured into water. The product is extracted into EtOAc (2×). The combined organics are dried (MgSO4), filtered and concentrated. Purification via flash chromatography (12 g silica gel, 0-5% MeOH/CH2Cl2) affords the title compound (40 mg, 17%). LCMS (ESMS): m/z 465.20 (M++1)

Workup

  1. customThe reaction
  2. customvial is sealed
  3. temperatureAfter this time the reaction is cooled
  4. extractionThe product is extracted into EtOAc (2×)
  5. dry with materialThe combined organics are dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification via flash chromatography (12 g silica gel, 0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-52d447007daa442c816d9e43b3651f0b
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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