1H-Indole-7-carboxylic acid → HCID 69513484, compound

HRID 855344Notes

Reaction equation

HRID 855344 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:65]=[CH:64][C:51]([CH2:52][NH:53][CH2:54][CH2:55][CH:56]([C:58]2[O:59][C:60]([CH3:63])=[CH:61][CH:62]=2)[CH3:57])=[CH:50][CH:49]=1)([CH3:47])([CH3:46])[CH3:45]>CN(C=O)C.O>[C:44]([C:48]1[CH:65]=[CH:64][C:51]([CH2:52][N:53]([CH2:54][CH2:55][CH:56]([C:58]2[O:59][C:60]([CH3:63])=[CH:61][CH:62]=2)[CH3:57])[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)([CH3:46])([CH3:45])[CH3:47]

Participants

7

Reactant 4

HCID 742811H-Indole-7-carboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69342909HCID 69342909, compound

Product 1

HCID 69513484HCID 69513484, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 48 mg (0.3 mmol) of 1H-indole-7-carboxylic acid and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 90 mg (0.3 mmol) of [rac]-(4-tert-butyl-benzyl)-[3-(5-methyl-furan-2-yl)-butyl]-amine in 1 ml DMF were added. After stirring for 2 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The orange residue was purified by column chromatography (8 g silica gel; heptane/EtOAc 6:1) to give 87 mg (63%) of a colorless viscous oil. MS (ISP) 443.5 (M+H)+.

Workup

  1. stirringAfter stirring for 2 h at rt
  2. extractionextracted with 2×50 ml 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 orange residue was purified by column chromatography (8 g silica gel; heptane/EtOAc 6:1)

Sources & evidence

ORD record
ord-c2125880dc1c4ea0b025929e1c7439d6
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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