2-Thiophenecarboxylic acid → HCID 57901607, compound

HRID 1851493Notes

Reaction equation

HRID 1851493 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21](O)=[O:22].C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(OCC)(=O)C.CN(C)C=O>[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2)=[O:22]

Participants

7

Reactant 4

HCID 107002-Thiophenecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 111381941H-Indole-2-carboxylic acid, 7-amino-, ethyl ester

Product 1

HCID 57901607HCID 57901607, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 7-amino-1H-indole-2-carboxylate (0.40 g), thiophene-2-carboxylic acid (0.28 g), ethyldiisopropylamine (0.75 mL), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.82 g) and N,N-dimethylformamide (10 mL) was stirred at 60° C. for 18 hr. The reaction mixture was diluted with ethyl acetate, washed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=3:97-3:7) to give the title compound (510 mg, yield 83%) as a pale-yellow amorphous solid.

Workup

  1. washwashed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-54e6bd638db54838ae583cd7335f4987
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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