Ammonium formate → N-(2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-6-yl)-N-methylamine

HRID 2068882Notes

Reaction equation

HRID 2068882 reaction equation
[CH3:1][C:2]1([CH3:48])[CH2:10][C:9]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:7]=[C:6]([C:19]3[N:20]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[C:23]([N:28](C)[C:29](=O)OCC3C=CC=CC=3)[CH:22]=4)[C:5]=2[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>C(O)C.[C].[Pd]>[CH3:1][C:2]1([CH3:48])[CH2:10][C:9]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[N:7]=[C:6]([C:19]3[N:20]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:46])([CH3:45])[CH3:47])[C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[C:23]([NH:28][CH3:29])[CH:22]=4)[C:5]=2[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58550230benzyl N-(2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-6-yl)-N-methylcarbamate

Product 1

HCID 58550308N-(2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-6-yl)-N-methylamineYield 81.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of benzyl N-(2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-6-yl)-N-methylcarbamate (2.2 g, 3.1 mmol), 10% palladium-carbon (216 mg) and ammonium formate (989 mg, 16 mmol) in ethanol (30 ml) was heated under reflux for 2.5 hr. After cooling, the reaction mixture was filtered through celite, and the filtrate was concentrated. The residue was purified by silica gel chromatography to give the title compound (1.4 g, yield 79%).

Workup

  1. temperatureunder reflux for 2.5 hr
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-dd8c39d74c42466b9c9d1eb9f11718c5
Source dataset
uspto-grants-2012_10
Patent number
US08299070B2

Reaction notes

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