Triethylamine → HCID 58834671, compound

HRID 1443823Notes

Reaction equation

HRID 1443823 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[Br:6][C:7]1[CH:15]=[C:14]([C:16](O)=[O:17])[CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[OH:5][CH2:4][CH2:3][CH2:2][NH:1][C:16]([C:14]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[C:7]([Br:6])[CH:15]=1)=[O:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 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 58834671HCID 58834671, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Aminopropanol (1.36 g, 18.1 mmol) was added to a solution of 4-bromo-1H-indole-6-carboxylic acid (4.35 g, 18.1 mmol), triethylamine (4.60 mL, 45.3 mmol), and O-benzotriazol-1-yl-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (HBTU) (6.87 g, 18.1 mmol) in DMF (40 mL) and stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and purified by column chromatography (10% methanol in dichloromethane) to yield 3.0 g (56%) of 4-bromo-1H-indole-6-carboxylic acid (3-hydroxy-propyl)-amide. Mass spectrum (LCMS, ESI pos.): Calcd for C12H13BrN2O2 296.02. Found 296.9; (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e8f4c36844bd4be0a046f1cd19b3e99e
Source dataset
uspto-grants-2010_02
Patent number
US07662824B2

Reaction notes

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