Sodium Carbonate → (E)-3-{1-[4'-(2-Morpholin-4-yl-ethyl)-biphenyl-3-sulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide

HRID 1445495Notes

Reaction equation

HRID 1445495 reaction equation
Br[C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:36]2[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[CH:38][CH:37]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[N:44]1([CH2:43][CH2:42][C:39]2[CH:40]=[CH:41][C:36]([C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([N:11]4[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:20][O:21][CH:22]5[CH2:27][CH2:26][CH2:25][CH2:24][O:23]5)=[O:19])=[CH:12]4)(=[O:10])=[O:9])[CH:3]=3)=[CH:37][CH:38]=2)[CH2:45][CH2:46][O:47][CH2:48][CH2:49]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 44392864-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenethyl)morpholineHCID 86621698(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

Product 1

HCID 86621697(E)-3-{1-[4'-(2-Morpholin-4-yl-ethyl)-biphenyl-3-sulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamideYield 85.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (7.60 g) and 4-{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-morpholin (8.00 g) are dissolved in DME (300 mL). (Ph3P)3PdCl2 (2.40 g) and a 2M Na2CO3-solution (25 mL) are added and the mixture is heated 5 h to reflux temperature under an inert gas atmosphere. The reaction mixture is filtered and evaporated. After addition of a NaHCO3-solution and ethyl acetate, the organic phase is dried and evaporated. The crude product is purified by silica gel flash chromatography. 8.1 g of the title compound are obtained.

Workup

  1. temperaturethe mixture is heated 5 h
  2. temperatureto reflux temperature under an inert gas atmosphere
  3. filtrationThe reaction mixture is filtered
  4. customevaporated
  5. additionAfter addition of a NaHCO3-solution and ethyl acetate
  6. customthe organic phase is dried
  7. customevaporated
  8. customThe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-e3de3eb83c024df99e37a2d87eacdcf0
Source dataset
uspto-grants-2010_02
Patent number
US07666868B2

Reaction notes

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