Water → hydroxy-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-acetic acid methyl ester

HRID 886560Notes

Reaction equation

HRID 886560 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[N:7]=1)[OH:5].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[C:30]2[C:25](=[N:26][CH:27]=[C:28](B3OC(C)(C)C(C)(C)O3)[CH:29]=2)[N:24]([S:40]([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=2)(=[O:42])=[O:41])[CH:23]=1.O>O1CCCC1.C(#N)C>[CH3:1][O:2][C:3](=[O:13])[CH:4]([OH:5])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:28]2[CH:29]=[C:30]3[C:22]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[O:15][CH3:14])=[CH:23][N:24]([S:40]([C:43]4[CH:44]=[CH:45][C:46]([CH3:49])=[CH:47][CH:48]=4)(=[O:42])=[O:41])[C:25]3=[N:26][CH:27]=2)[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 160390673-(2-Methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 59825086Methyl 2-(6-bromopyridin-2-yl)-2-hydroxyacetate

Product 1

HCID 59825111hydroxy-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-acetic acid methyl esterYield 32.8%

Reagents, catalysts & solvents 1

HCID 22177404Acetonitrile tetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

In a microwave vial (6-bromo-pyridin-2-yl)-hydroxy-acetic acid methyl ester (430.9 mg, 1.75 mmol), 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 (1.00 g, 1.75 mmol) in tetrahydrofuran/acetonitrile/1 N aqueous sodium bicarbonate (20 ml) was degassed with nitrogen and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichloromethane adduct (143.0 mg, 0.18 mmol) was added and the vial sealed. This reaction mixture was heated to 80° C. for 30 minutes in a microwave reactor. 100 ml water was added and this mixture was extracted with ethyl acetate (3×) the combined organic layers were dried over magnesium sulfate and purified by silica gel chromatography to yield hydroxy-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-acetic acid methyl ester as a white solid (312 mg, 32% yield). MS: m/z 544.5 (M+H+).

Workup

  1. additionwas added
  2. extractionthis mixture was extracted with ethyl acetate (3×) the combined organic layers
  3. dry with materialwere dried over magnesium sulfate
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f94065e266b14839891e496892138b75
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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