Pyrrolidine → HCID 59334985, compound

HRID 1510326Notes

Reaction equation

HRID 1510326 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[C:4]([C:14]([OH:16])=O)=[CH:3]1.[CH:17]([N:20]([CH:23]([CH3:25])C)CC)([CH3:19])C.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.F[B-](F)(F)F.N1CCCC1>CN(C)C=O.C(OCC)(=O)C.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[C:4]([C:14]([N:20]2[CH2:17][CH2:19][CH2:25][CH2:23]2)=[O:16])=[CH:3]1

Participants

8

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59334938HCID 59334938, compound

Product 1

HCID 59334985HCID 59334985, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

400 mg of 1-methyl-6-nitro-1H-indole-3-carboxylic acid are dissolved in 4 ml dimethylformamide, combined with 774 μl N,N-diisopropyl-N-ethyl-amine as well as 583 mg O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium-tetrafluoroborate (TBTU) and stirred for 45 minutes at ambient temperature. 225 μl of pyrrolidine are added and the mixture is stirred for 5 hours at ambient temperature. Then it is divided between water and ethyl acetate, the organic phase is washed with saturated sodium chloride solution and dried on magnesium sulphate. The solvents are eliminated in vacuo.

Workup

  1. stirringthe mixture is stirred for 5 hours at ambient temperature
  2. washthe organic phase is washed with saturated sodium chloride solution
  3. customdried on magnesium sulphate

Sources & evidence

ORD record
ord-410bd81e2b1c4ea4ac8c74a98f704e0a
Source dataset
uspto-grants-2012_07
Patent number
US08211923B2

Reaction notes

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