Diisopropylethylamine → HCID 59657535, compound

HRID 2055548Notes

Reaction equation

HRID 2055548 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]([OH:14])=O)=[C:7]([CH3:11])[NH:8]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[NH:46]1[CH2:51][CH2:50][C:49]2([C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH2:53][O:52]2)[CH2:48][CH2:47]1>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]([N:46]3[CH2:51][CH2:50][C:49]4([C:59]5[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=5[CH2:53][O:52]4)[CH2:48][CH2:47]3)=[O:14])=[C:7]([CH3:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 104424983H-spiro[2-benzofuran-1,4'-piperidine]HCID 451210656-Chloro-2-methyl-1H-indole-3-carboxylic acid

Product 1

HCID 59657535HCID 59657535, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.040 g (0.19 mmol) 6-chloro-2-methyl-1H-indole-3-carboxylic acid, 0.069 ml (0.40 mmol) N,N-diisopropylethylamine and 0.061 g (0.19 mmol) 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate in 1 ml dry N,N-dimethylformamide were added 0.036 g (0.19 mmol) spiro[isobenzofuran-1(3H), 4′-piperidine] at room temperature. After stirring for 1 h the reaction mixture was quenched with 0.5 M aqueous sodium hydroxide solution (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with water (2×30 ml) and brine (1×30 ml), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (n-heptane/ethyl acetate) to give the title compound (0.036 g, 49%) as a white solid.

Workup

  1. customwas quenched with 0.5 M aqueous sodium hydroxide solution (20 ml)
  2. extractionextracted with ethyl acetate (2×30 ml)
  3. washThe combined organic layers were washed with water (2×30 ml) and brine (1×30 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (n-heptane/ethyl acetate)

Sources & evidence

ORD record
ord-6525a800472c43e096e2ab6479552074
Source dataset
uspto-grants-2008_02
Patent number
US07332501B2

Reaction notes

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