HCID 790306, compound → HCID 87550140, compound

HRID 1895996Notes

Reaction equation

HRID 1895996 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[N:3]=1.[C:17]1([NH:23][C:24]([C:26]2[O:27][C:28](Br)=[CH:29][CH:30]=2)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[CH3:1][C:2]1[N:3]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:12][CH2:13][N:14]([C:28]3[O:27][C:26]([C:24]([NH:23][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:25])=[CH:30][CH:29]=3)[CH2:15][CH2:16]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 790306HCID 790306, compoundHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 87550140HCID 87550140, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A well homogenised mixture of the Compound of Example 3 (100 mg, 0.47 mmol) and N-phenyl-5-bromofuran-2-carboxamide (125 mg, 0.47 mmol) was stirred at 120° C. for 8 h. The reaction mixture was poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography eluting with Petroleum Ether-EtOAc 7:3, affording the title product (36 mg) as a brown solid.

Workup

  1. stirringwas stirred at 120° C. for 8 h
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. customdried on Na2SO4
  5. customevaporated to dryness in vacuo
  6. customto afford a residue, which
  7. customwas purified by flash chromatography
  8. washeluting with Petroleum Ether-EtOAc 7:3

Sources & evidence

ORD record
ord-309a3ca12d9743ecba9910e42d2b133c
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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