Diisopropylethylamine → Propyl [7-(4-benzyl-1H-1,2,3-triazol-1-yl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetate

HRID 1944016Notes

Reaction equation

HRID 1944016 reaction equation
[N:1]([CH:4]1[CH2:23][N:8]2[C:9]3[C:14]([C:15]([CH2:16][C:17]([O:19][CH2:20][CH2:21][CH3:22])=[O:18])=[C:7]2[CH2:6][CH2:5]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N+:2]=[N-:3].[CH2:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:25]#[CH:26].C(N(C(C)C)CC)(C)C>O1CCCC1.[Cu]I>[CH2:24]([C:25]1[N:3]=[N:2][N:1]([CH:4]2[CH2:23][N:8]3[C:9]4[C:14]([C:15]([CH2:16][C:17]([O:19][CH2:20][CH2:21][CH3:22])=[O:18])=[C:7]3[CH2:6][CH2:5]2)=[CH:13][CH:12]=[CH:11][CH:10]=4)[CH:26]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 575753BenzylacetyleneHCID 59487226Propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate

Product 1

HCID 86645391Propyl [7-(4-benzyl-1H-1,2,3-triazol-1-yl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate (1 eq) (Synthesis described in WO07019675 A1) and prop-2-yn-1-ylbenzene (2 eq) in tetrahydrofuran (THF) (0.1M) at room temperature was added diisopropyl ethylamine (DIPEA) (5 eq) and CuI (5 eq). The reaction mixture was stirred overnight then quenched with NH4Cl sat and extracted with ethyl acetate (EA), washed with brine, dried over Na2SO4 and evaporated. Purification by combi-flash EA/Hex 0-100% afforded the desired compound which was used directly for next step.

Workup

  1. customthen quenched with NH4Cl
  2. extractionextracted with ethyl acetate (EA)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customPurification by combi-flash EA/Hex 0-100%

Sources & evidence

ORD record
ord-968e6740638a412e9dbe8b972029b298
Source dataset
uspto-grants-2013_03
Patent number
US08394819B2

Reaction notes

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