1H-Indole-7-carboxylic acid → HCID 69346543, compound

HRID 855412Notes

Reaction equation

HRID 855412 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.[C:44]([C:48]1[CH:62]=[CH:61][C:51]([CH2:52][NH:53][CH2:54][CH:55]([OH:60])[C:56]([F:59])([F:58])[F:57])=[CH:50][CH:49]=1)([CH3:47])([CH3:46])[CH3:45]>CN(C=O)C.O>[C:44]([C:48]1[CH:62]=[CH:61][C:51]([CH2:52][N:53]([CH2:54][CH:55]([OH:60])[C:56]([F:59])([F:57])[F:58])[C:10]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[NH:1][CH:2]=[CH:3]3)=[O:12])=[CH:50][CH:49]=1)([CH3:47])([CH3:45])[CH3:46]

Participants

7

Reactant 4

HCID 742811H-Indole-7-carboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69342808HCID 69342808, compound

Product 1

HCID 69346543HCID 69346543, compoundYield 21.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 30 mg (0.19 mmol) of 1H-indole-7-carboxylic acid and 60 mg of TBTU (0.19 mmol) in 6 ml DMF, were added 0.16 ml (0.93 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 85 mg (0.19 mmol) of [rac]-(4-tert-butyl-benzyl)-(3,3,3-trifluoro-2-hydroxy-propyl)-amine were added. After stirring for 4 h at rt, the reaction mixture was diluted with 60 ml water and extracted with EtOAc (2×). 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 (9 g silica gel; EtOAc/heptane 1:4) to give 17 mg white solid (17%). MS (EI) 418.2 (M)+.

Workup

  1. stirringAfter stirring for 4 h at rt
  2. extractionextracted with EtOAc (2×)
  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 (9 g silica gel; EtOAc/heptane 1:4)

Sources & evidence

ORD record
ord-a685b0fd096b48b1a506c75eb9d37b20
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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