HCID 86676260, compound → HCID 71237051, compound

HRID 1045790Notes

Reaction equation

HRID 1045790 reaction equation
[N:1]([CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]2[CH:15]=[CH:16][CH:17]=[N:18][C:7]=2[N:6]([CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C:5]1=[O:29])=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]2[CH:15]=[CH:16][CH:17]=[N:18][C:7]=2[N:6]([CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:27])([CH3:26])[CH3:28])([CH3:23])[CH3:24])[C:5]1=[O:29]

Participants

4

Reactant 1

HCID 86676260HCID 86676260, compound

Product 1

HCID 71237051HCID 71237051, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add palladium/carbon (2.2 g, 1.0 mmol, 5% on carbon) to a nitrogen purged solution of 7-azido-5-[2-(tert-butyl(dimethyl)silyl)oxyethyl]-7H-pyrido[2,3-d][3]benzazepin-6-one (39.8 g, 92.3 mmol) in ethanol (923 mL). Evacuate/fill with hydrogen three times and stir under hydrogen (one atmosphere) at ambient temperature overnight. Filter over Celite®, rinse with ethanol and ethyl acetate and concentrate to obtain the title compound as a transparent oil (36.6 g, 89.9 mmol, 97%). MS (m/z): 384 (M+1).

Workup

  1. customEvacuate/fill with hydrogen three times
  2. filtrationFilter over Celite®
  3. washrinse with ethanol and ethyl acetate
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-b6fc24af4acb4880a20ca1b8a67016e7
Source dataset
uspto-grants-2013_10
Patent number
US08569286B2

Reaction notes

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