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

HRID 2408448

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:51]=[CH:50][C:39]([O:40][CH2:41][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][CH2:41][O:40][C:39]2[CH:50]=[CH:51][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)[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1

Participants

Conditions

Temperature: 100 °C

Procedure

(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (4.6 g) and 4-{3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-propyl}-morpholine (3.9 g) are dissolved in DME (200 mL). Under an inert gas atmosphere are added are added (Ph3P)3PdCl2 (1.4 g) and 2M Na2CO3-solution (31 mL). The mixture is heated to 100° C. for 2 h. After filtration and extraction, the crude product from the organic phase is purified by silica gel flash chromatography. 4.7 g of the title compound are obtained as brownish oil.

Workup

additionUnder an inert gas atmosphere are added
filtrationAfter filtration and extraction
customthe crude product from the organic phase is purified by silica gel flash chromatography

Sources & evidence

ORD record: ord-0c3a7d2f3ab5490e93a1cd915c6059e3
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815855B2

Linked notes

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