Diethylamine → HCID 19010539, compound

HRID 1741732Notes

Reaction equation

HRID 1741732 reaction equation
BrC1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[CH:16][N:15]=1)[CH2:6][CH2:5]2.[CH2:27]([OH:31])[CH2:28][C:29]#[CH:30].[CH2:32](NCC)C>CCOC(C)=O>[OH:31][CH:27]([CH3:32])[C:28]#[C:29][C:30]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)=[CH:16][N:15]=1)[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 135663-Butyn-1-OLHCID 19010524HCID 19010524, compound

Product 1

HCID 19010539HCID 19010539, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-bromo-2-{[5-(4-fluorophenyl)-2-pyridyl]methyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline (500 mg, 1.22 mmol) and 3-butyn-1-ol (170 mg, 0.19 mL, 2.44 mmol) in diethylamine (20 mL) is de-gassed with argon. After 20 minutes, pallasium bis(diphenylphosphino) chloride (85 mg, 0.12 mmol) and cuprous iodide (13 mg, 0.12 mmol) are added and the resulting solution is stirred at ambient temperature for 12 hours. The reaction mixture is then diluted with EtOAc (20 mL), dried over MgSO4, filtered through celite and concentrated in vacuo. The residue is chromatographed (silica gel, 1:1 then 2:1 EtOAc/hexanes) to afford 6-[3-hydroxy-1-butyn-1-yl]-2-{[5-(4-fluorophenyl)-2-pyridyl]-methyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline as yellow oil.

Workup

  1. dry with materialdried over MgSO4
  2. filtrationfiltered through celite and
  3. concentrationconcentrated in vacuo
  4. customThe residue is chromatographed (silica gel, 1:1

Sources & evidence

ORD record
ord-c933b3b67a5241fdb86467141d6b3266
Source dataset
uspto-grants-1994_08
Patent number
US05334600

Reaction notes

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