HCID 23398221, compound → HCID 66849220, compound

HRID 1406419Notes

Reaction equation

HRID 1406419 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:26]1[C:27](=[O:43])[N:28]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[CH:29]=[C:30]([N+:32]([O-:34])=[O:33])[CH:31]=1>CCCCCC>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:26]1[C:27](=[O:43])[N:28]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:41])([CH3:40])[CH3:42])[CH:29]=[C:30]([N+:32]([O-:34])=[O:33])[CH:31]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 23398221HCID 23398221, compoundHCID 581174113-iodo-5-nitro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyridin-2-one2×

Product 1

HCID 66849220HCID 66849220, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The title compound was prepared by the route outlined in Scheme 11 and using the experimental from Example 37, Step 3, with intermediate 5-(tert-butyl-dimethyl-silanyloxy)-indole-1-carboxylic acid tert-butyl ester (11a) (2.90 g, 8.3 mmol) and (6a), 3-iodo-5-nitro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyridin-2-one (3 g, 7.6 mmol). The resultant crude product was purified by flash chromatography on SiO2 with hexane—20% ethyl acetate/hexane (gradient) to afford after trituration using hexane, the title compound as a pale yellow solid, 3.67 g, 79%.

Workup

  1. customThe title compound was prepared by the route
  2. customThe resultant crude product was purified by flash chromatography on SiO2 with hexane—20% ethyl acetate/hexane (gradient)
  3. customto afford after trituration

Sources & evidence

ORD record
ord-56d5a9e1311f4306b5956b73b44e2a70
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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