Potassium Carbonate → Carbamic acid, N-[[3-[4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]phenyl]methyl]-, 1,1-dimethylethyl ester

HRID 1625484Notes

Reaction equation

HRID 1625484 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=2)[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])O1.Br[C:26]1[C:34]2[C:29](=[N:30][CH:31]=[CH:32][C:33]=2[Cl:35])[N:28]([S:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:38])=[O:37])[CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>>[Cl:35][C:33]1[CH:32]=[CH:31][N:30]=[C:29]2[N:28]([S:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)(=[O:38])=[O:37])[CH:27]=[C:26]([C:9]3[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=3)[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C:34]=12

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 2760591tert-Butyl {[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}carbamateHCID 497589583-Bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Product 1

HCID 59362517Carbamic acid, N-[[3-[4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]phenyl]methyl]-, 1,1-dimethylethyl esterYield 40.4%

Conditions

Temperature
90 °C

Procedure

tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate (333 mg, 1.0 mmol), 3-bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (372 mg, 1.0 mmol), potassium carbonate (270 mg, 2 mmol) and PdCl2(dppf)CH2Cl2 (41 mg, 0.05 mmol) were added to a reaction flask which was purged thoroughly with N2. 10 ml of dried dioxane was added via syringe and the reaction was heated to 90° C. for overnight. After LC-MS showed the reaction was complete, the solution was then cooled to room temperature and filtered and concentrated. The residue was purified by chromatography (0-50% EtOAc:hexane), giving 201 mg of tert-butyl 3-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzylcarbamate as a white solid, yield: 40.4%.

Workup

  1. customwas purged thoroughly with N2
  2. addition10 ml of dried dioxane was added via syringe
  3. temperaturethe solution was then cooled to room temperature
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (0-50% EtOAc:hexane)

Sources & evidence

ORD record
ord-60e00d3f45914b76b3573f216e18285a
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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