1,3-Dihydro-5-nitro-1'-((2-(trimethylsilyl)ethoxy)methyl)spiro(2H-indene-2,3'-(3H)pyrrolo(2,3-b)pyridin)-2'(1'H)-one → 5-amino-1'-((2-(trimethylsilyl)ethoxy)methyl)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 1094070Notes

Reaction equation

HRID 1094070 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:27](=[CH:28][CH:29]=1)[CH2:26][C:8]1([C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:9]1=[O:25])[CH2:7]2)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:27](=[CH:28][CH:29]=1)[CH2:26][C:8]1([C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:23])[CH3:24])[C:9]1=[O:25])[CH2:7]2

Participants

4

Reactant 1

HCID 591667381,3-Dihydro-5-nitro-1'-((2-(trimethylsilyl)ethoxy)methyl)spiro(2H-indene-2,3'-(3H)pyrrolo(2,3-b)pyridin)-2'(1'H)-one

Product 1

HCID 591667205-amino-1'-((2-(trimethylsilyl)ethoxy)methyl)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 10% Pd/C (3 g) and (±)-5-nitro-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one from Step A (19.1 g, 46.4 mmol) was stirred vigorously in EtOH (400 mL) under an atmosphere of hydrogen (ca. 1 atm). After 18 h, the mixture was filtered through a pad of Celite, washing extensively with MeOH, and the filtrate was concentrated to give the crude racemic compound. The enantiomers were resolved by HPLC, utilizing a Chiralcel OD column and eluting with MeOH. The first major peak to elute was (−)-5-amino-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one, the title compound, and the second major peak to elute was (+)-5-amino-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one. MS: m/z=382 (M+1).

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. washwashing extensively with MeOH
  3. concentrationthe filtrate was concentrated
  4. customto give the crude racemic compound
  5. washeluting with MeOH
  6. washThe first major peak to elute
  7. washthe title compound, and the second major peak to elute

Sources & evidence

ORD record
ord-a7c9eb798e21421dbf820a98fa263221
Source dataset
uspto-grants-2012_03
Patent number
US08133891B2

Reaction notes

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