1H-Indole-7-carboxylic acid → HCID 69347301, compound

HRID 855414Notes

Reaction equation

HRID 855414 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([OH:12])=O)[CH:3]=[CH:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH2:44]([NH:48][CH2:49][C:50]1[CH:55]=[CH:54][C:53]([C:56]([CH3:59])([CH3:58])[CH3:57])=[CH:52][CH:51]=1)[CH2:45][CH2:46][CH3:47]>CN(C=O)C.O>[CH2:44]([N:48]([CH2:49][C:50]1[CH:55]=[CH:54][C:53]([C:56]([CH3:57])([CH3:59])[CH3:58])=[CH:52][CH:51]=1)[C:10]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH:2]=[CH:3]2)=[O:12])[CH2:45][CH2:46][CH3:47]

Participants

7

Reactant 4

HCID 742811H-Indole-7-carboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22159590HCID 22159590, compound

Product 1

HCID 69347301HCID 69347301, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 110 mg of 1H-indole-7-carboxylic acid (0.68 mmol) and 220 mg of TBTU (0.68 mmol) in 10 ml DMF, were added 0.59 ml (3.42 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 150 mg (0.68 mmol) of butyl-(4-tert-butyl-benzyl)-amine were added. After stirring for 2 h at rt, the reaction mixture was diluted with 100 ml water and extracted twice with EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; heptane/EtOAc 2:1) to give 209 mg (82%) of a light yellow viscous oil. MS (EI) 362.2 (M)+.

Workup

  1. stirringAfter stirring for 2 h at rt
  2. extractionextracted twice with EtOAc
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (8 g silica gel; heptane/EtOAc 2:1)

Sources & evidence

ORD record
ord-7595515125224fb1b6be0d276129f7a2
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

Loading…