Triethylamine → HCID 58834669, compound

HRID 1443826Notes

Reaction equation

HRID 1443826 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Br:8][C:9]1[CH:17]=[C:16]([C:18]([OH:20])=O)[CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:8][C:9]1[CH:17]=[C:16]([C:18]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[O:20])[CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 247286084-Bromo-1H-indole-6-carboxylic acid

Product 1

HCID 58834669HCID 58834669, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Methyl-piperazine (0.21 g, 2.1 mmol) was added to a solution of 4-bromo-1H-indole-6-carboxylic acid (0.50 g, 2.1 mmol), triethylamine (0.43 mL, 3.1 mmol) and HBTU (0.78 g, 2.1 mmol) in DMF (5 mL) and stirred at room temperature overnight. Reaction mixture was concentrated in vacuo and purified by column chromatography (10% methanol in dichloromethane) to yield 0.30 g (45%) of (4-bromo-1H-indol-6-yl)-(4-methyl-piperazin-1-yl)-methanone. Mass spectrum (LCMS, ESI pos.): Calcd for C14H16BrN3O: 321.05. Found 322.0 ; (M+H).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompurified by column chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-afbe9b4308ef48e18e33f05c521ec51a
Source dataset
uspto-grants-2010_02
Patent number
US07662824B2

Reaction notes

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