Cesium carbonate → HCID 71061452, compound

HRID 2201765

Reaction equation

HRID 2201765 reaction equation
Br[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:17]1([C:21]([NH2:23])=[O:22])[CH2:20][CH2:19]C1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[NH:8]1[C:7]2=[C:2]([NH:23][C:21]([CH:17]3[CH2:20][CH2:19]3)=[O:22])[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 1274476Cyclobutanecarboxamide2×HCID 196964567-Bromo-6-azaindole

Product 1

HCID 71061452HCID 71061452, compoundYield 39.3%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 7-bromo-1H-pyrrolo[2,3-c]pyridine (500 mg, 2.53 mmol) in toluene were added tris (dibenzylidene acetone)dipalladium (116.20 mg, 0.126 mmol), Xantphos (32.98 mg, 0.057 mmol), cesium carbonate (896 mg, 2.75 mmol), and cyclobutanecarboxamide (251 mg, 2.96 mmol, Intermediate 4). The resulting reaction mixture was heated to 120° C. and stirred for 8 hours. After cooling to room temperature a saturated aqueous sodium bicarbonate solution (20 mL) was added to the reaction mixture and extracted with ethyl acetate (3×50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography to afford N-(1H-pyrrolo[2,3-c]pyridin-7-yl)cyclopropane carboxamide (200 mg, 36% yield).

Workup

  1. customThe resulting reaction mixture
  2. additionwas added to the reaction mixture
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel (100-200) column chromatography

Sources & evidence

ORD record
ord-8b25761b28a245c19f0b2472249b7716
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Linked notes

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