Sodium Carbonate → [5-(4-{3-[(E)-2-(Tetrahydro-pyran-2-yloxycarbamoyl)-vinyl]-pyrrole-1-sulfonyl}-phenyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 2408443Notes

Reaction equation

HRID 2408443 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)=[O:19])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:28]([O:32][C:33](=[O:50])[NH:34][C:35]1[CH:40]=[CH:39][C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][N:36]=1)([CH3:31])([CH3:30])[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>O>[C:28]([O:32][C:33](=[O:50])[NH:34][C:35]1[CH:40]=[CH:39][C:38]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([N:11]3[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18](=[O:19])[NH:20][O:21][CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][O:23]4)=[CH:12]3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:37][N:36]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 17750222tert-butyl N-(5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamateHCID 86621691(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

Product 1

HCID 86621694[5-(4-{3-[(E)-2-(Tetrahydro-pyran-2-yloxycarbamoyl)-vinyl]-pyrrole-1-sulfonyl}-phenyl)-pyridin-2-yl]-carbamic acid tert-butyl esterYield 81.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (0.95 g) and [5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-carbamic acid tert-butyl ester (1.00 g) are dissolved under an inert gas atmosphere in dimethylethylenglycole (35 mL), and Pd(PPh3)3Cl2 (0.22 g) and a sodium carbonate solution (2.21 g dissolved in 21 water) is added and it is heated for 0.5 h at 90° C. After cooling the mixture is diluted with water, extracted with chloroform, and the combined organic phases are dried and evaporated. The residue is purified by silica gel flash chromatography CHCl3/THF (4:1). 0.97 g of the title compound are obtained with a melting point of 140-146° C.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted with chloroform
  3. customthe combined organic phases are dried
  4. customevaporated
  5. customThe residue is purified by silica gel flash chromatography CHCl3/THF (4:1)

Sources & evidence

ORD record
ord-fbda8e28a8d44d81bed3c85554a071de
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

Loading…