Potassium Carbonate → HCID 58542014, compound

HRID 1966668Notes

Reaction equation

HRID 1966668 reaction equation
[C:1]([NH:5][C:6]1[C:7]([NH2:21])=[CH:8][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:10][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:23]1[CH:24]=[C:25]2[CH2:31][CH2:30][NH:29][C:26]2=[N:27][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([NH:5][C:6]1[C:7]([NH2:21])=[CH:8][C:9]([C:23]2[CH:24]=[C:25]3[CH2:31][CH2:30][NH:29][C:26]3=[N:27][CH:28]=2)=[CH:10][CH:11]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 219640795-Bromo-2,3-dihydro-7-azaindoleHCID 58541900HCID 58541900, compound

Product 1

HCID 58542014HCID 58542014, compoundYield 28.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

In a microwave vial are added N1-tert-Butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzene-1,2-diamine (100 mg, 0.5 mmol) and 5-bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (180 mg, 0.62 mmol), tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol) and K2CO3 (139 mg, 1 mmol) in DMF (4 mL) and H2O (0.2 mL). The reaction mixture is heated at 110° C. in a microwave reactor for 1 hour. The reaction is cooled down to room temperature, poured into H2O (10 mL) and extracted with EtOAc (3×10 mL). The combined organic layer is dried (MgSO4), filtered and concentrated. The residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 to afford the title intermediate (40 mg, 28%). LCMS (ESMS): m/z 283.20 (M++1)

Workup

  1. temperatureThe reaction is cooled down to room temperature
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic layer is dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel flash column chromatography
  7. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-9d00a9c26a874d5fb4714aa481938abe
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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