HCID 59441760, compound → HCID 59441624, compound

HRID 1014397Notes

Reaction equation

HRID 1014397 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([N+:15]([O-])=O)[CH:13]=2)[CH2:8][C@H:7]1[CH3:20])=[O:5]>[Pd].CO>[CH3:21][N:2]([CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([NH2:15])[CH:13]=2)[CH2:8][C@H:7]1[CH3:20])=[O:5])[CH3:1]

Participants

4

Reactant 1

HCID 59441760HCID 59441760, compound

Product 1

HCID 59441624HCID 59441624, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

10% palladium on carbon (0.25 g, 8.52 mmol) was placed under N2 atm. MeOH (10 mL) was added, followed by a solution of N,N-dimethyl-2-[(2R)-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethanamine (2.92 g, 9.96 mmol) in MeOH (190 mL). The slurry was purged with N2, then was placed under H2 atm via a rubber balloon and maintained at rt for 2 days. The resulting mixture was filtered through a pad of Celite and the filtrate was concentrated. The oily residue was taken up into Et2O and concentrated again to obtain (2R)-1-[(dimethylamino)acetyl]-2-methyl-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine as a beige solid (2.43 g, 93%). 1H NMR (400 MHz, DMSO-d8) δ ppm 1.17 (d, J=5.86 Hz, 3H), 2.26 (s, 6H), 2.44 (d, J=14.83 Hz, 1H), 3.02 (d, J=14.28 Hz, 1H), 3.10-3.27 (m, 1H), 3.36 (d, J=14.28 Hz, 1H), 3.72 (s, 3H), 4.52-4.77 (m, 3H), 6.72 (s, 1H), 7.48 (s, 1H); ESIMS (M+H)+=264.23.

Workup

  1. customThe slurry was purged with N2
  2. filtrationThe resulting mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated
  4. concentrationconcentrated again

Sources & evidence

ORD record
ord-4587e511c2d04435bba5c13f219ec731
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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