4-Methylmorpholine → Ethyl 3-(6-{2-[6-(methylamino)-2-pyridyl]ethoxy}benzo[b]thiophen-3-yl)propanoate

HRID 985488Notes

Reaction equation

HRID 985488 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][S:7][C:6]=2[CH:17]=1.CN1CCOCC1.[CH3:25][NH:26][C:27]1[N:32]=[C:31]([CH2:33][CH2:34]O)[CH:30]=[CH:29][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:25][NH:26][C:27]1[N:32]=[C:31]([CH2:33][CH2:34][O:1][C:2]2[CH:3]=[CH:4][C:5]3[C:9]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][S:7][C:6]=3[CH:17]=2)[CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 105348582-[6-(Methylamino)-2-pyridyl]ethan-1-olHCID 11288155Ethyl 3-(6-hydroxybenzo[B]thiophen-3-YL)propanoate

Product 1

HCID 11234493Ethyl 3-(6-{2-[6-(methylamino)-2-pyridyl]ethoxy}benzo[b]thiophen-3-yl)propanoateYield 19.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(6-hydroxybenzo[b]thiophen-3-yl)propanoate (100 mg, 0.4 mmol) and 4-methylmorpholine (0.05 ml, 0.44 mmol) were dissolved in THF (5 ml) and stirred for 5 minutes. 2-[6-(Methylamino)-2-pyridyl]ethan-1-ol (91 mg, 0.6 mmol), triphenylphosphine (210 mg, 0.8 mmol) and diisopropyl azodicarboxylate (0.16 ml, 0.8 mmol) were added to the mixture sequentially. After stirring overnight under argon, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried with sodium sulfate, filtered and evaporated under vacuum. The crude product was chromatographed over silica gel to yield 30 mg (19%) of Ethyl 3-(6-{2-[6-(methylamino)-2-pyridyl]ethoxy}benzo[b]thiophen-3-yl)propanoate.

Workup

  1. stirringAfter stirring overnight under argon
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe crude product was chromatographed over silica gel

Sources & evidence

ORD record
ord-1938956dd736469da1c2ff0576ffed6f
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

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