Isobutylamine → HCID 70029876, compound

HRID 396199Notes

Reaction equation

HRID 396199 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:25](O)=[O:26])#[N:2].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH2:52]([NH2:56])[CH:53]([CH3:55])[CH3:54].C(N(C(C)C)CC)(C)C>CN(C)C=O.ClCCl>[CH2:52]([NH:56][C:25]([C:7]1[N:6]([CH2:5][CH2:4][CH2:3][C:1]#[N:2])[C:14]2[C:9]([CH:8]=1)=[CH:10][C:11]([O:15][CH2:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:24])=[CH:12][CH:13]=2)=[O:26])[CH:53]([CH3:55])[CH3:54]

Participants

7

Reactant 4

HCID 6558IsobutylamineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 23003155HCID 23003155, compound

Product 1

HCID 70029876HCID 70029876, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1-(3-Cyanopropyl)-5-(2,6-dichlorobenzyloxy)-1H-indole-2-carboxylic acid (0.10 g, 0.25 mmol), from Example 2(a), was dissolved in dimethylformamide (15 mL). PyBroP (bromo-tris-pyrrolidino-phosphonium hexafluorophosphate) (0.13 g, 0.27 mmol) was added followed by isobutylamine (0.054 g, 0.74 mmol), diisopropylethylamine (0.13 g, 0.99 mmol), and a catalytic amount of N,N-dimethylaminopyridine. The reaction mixture was stirred for 18 h under argon at ambient temperature. The solution was diluted with dichloromethane and washed with water (3X) and brine. The organic layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification by flash chromatography (silica gel, 30% ethyl acetate/hexanes) yielded a white solid (0.076 g, 67%). MS(ES) m/e 458.2 [M +H]+.

Workup

  1. washwashed with water (3X) and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customPurification by flash chromatography (silica gel, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8e3ba01b55ad40f1800139d762b52d31
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

Loading…