4-(Methanesulfonyl)phenylboronic acid → (2-Ethoxy-naphthalen-1-yl)-[3-(4-methanesulfonyl-phenyl)-pyrrolo[2,3-b]pyridin-1-yl]-methanone

HRID 1820896Notes

Reaction equation

HRID 1820896 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=2[O:23][CH2:24][CH3:25])=[O:12])[CH:3]=1.[CH3:26][S:27]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)(=[O:29])=[O:28]>O1CCCC1.C(=O)([O-])[O-].[K+].[K+].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>[CH2:24]([O:23][C:14]1[CH:15]=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]=1[C:11]([N:4]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[C:2]([C:33]2[CH:34]=[CH:35][C:30]([S:27]([CH3:26])(=[O:29])=[O:28])=[CH:31][CH:32]=2)=[CH:3]1)=[O:12])[CH3:25]

Participants

6

Reactant 2

HCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 497589133-Bromo-1-(2-ethoxy naphthoyl)-7-azaindole

Product 1

HCID 57891760(2-Ethoxy-naphthalen-1-yl)-[3-(4-methanesulfonyl-phenyl)-pyrrolo[2,3-b]pyridin-1-yl]-methanone

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
60 °C

Procedure

(3-Bromo-pyrrolo[2,3-b]pyridin-1-yl)-(2-ethoxy-naphthalen-1-yl)-methanone 85 (35 mg, 0.0088 mmol), 4-Methanesulfonyl-phenylboronic acid (35 mg, 0.18 mmol) and tetrakis(triphenylphosphine)palladium(0) (5 mg) were stirred in tetrahydrofuran (16 mL) and potassium carbonate solution (8.0 mL, 1 M aqueous). The reaction mixture was stirred over night at 60° C. The reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate and brine. The organic portion was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated and purified by flash chromatography (ethyl acetate:hexanes 20%-100%). The desired product, 84 was obtained as a pale yellow powder (10 mg, 20%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompartitioned between ethyl acetate and brine
  3. dry with materialThe organic portion was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash chromatography (ethyl acetate:hexanes 20%-100%)

Sources & evidence

ORD record
ord-49eebb93aa4f4d25af5bc8db85a5d876
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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