1H-Indole-5-Carboxylic Acid → HCID 67168639, compound

HRID 2170859Notes

Reaction equation

HRID 2170859 reaction equation
Cl.[Cl:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[NH:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25](O)=[O:26])=[CH:22][CH:23]=2)[CH:18]=[CH:17]1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[Cl:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:9][CH2:10][N:11]([C:25]([C:21]3[CH:20]=[C:19]4[C:24](=[CH:23][CH:22]=3)[NH:16][CH:17]=[CH:18]4)=[O:26])[CH2:12][CH2:13]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 742801H-Indole-5-Carboxylic AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 177497914-(4-Chlorophenoxy)piperidine hydrochloride

Product 1

HCID 67168639HCID 67168639, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-(4-chlorophenoxy)piperidine hydrochloride (300 mg, 1.21 mmol), 1H-indole-5-carboxylic acid (195 mg, 1.21 mmol), and N,N-diisopropylethylamine (0.85 mL, 4.84 mmol) in N,N-dimethylformamide (10 mL) was add HBTU (688 mg, 1.81 mmol) at room temperature. After stirring at 60° C. for 2 hours, the mixture was poured into water (50 mL). This was extracted with ethyl acetate (50 mL) and washed with water (50 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (NH-gel, eluting with n-hexane/ethyl acetate=1/1) to give 403 mg (94% yield) of the title compound as a white solid.

Workup

  1. extractionThis was extracted with ethyl acetate (50 mL)
  2. washwashed with water (50 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography (NH-gel, eluting with n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-5a3196fa23304d54ad69491addb8b8f3
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

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