tert-Butyldimethylsilyl chloride → 7-bromo-N-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-3-nitroquinolin-4-amine

HRID 221620Notes

Reaction equation

HRID 221620 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][C@@H:16]([CH3:19])[CH2:17][OH:18])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][C@@H:16]([CH3:19])[CH2:17][O:18][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 67157472(2S)-2-[(7-bromo-3-nitroquinolin-4-yl)amino]propan-1-ol

Product 1

HCID 671576277-bromo-N-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-3-nitroquinolin-4-amineYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of (2S)-2-[(7-bromo-3-nitroquinolin-4-yl)amino]propan-1-ol (30.0 g, 92.0 mmol) dissolved in 100 mL of anhydrous pyridine was treated with tert-butyldimethylsilyl chloride (15.2 g, 101.2 mmol) and a catalytic amount of DMAP (112 mg, 0.92 mmol). After stirring overnight at ambient temperature under an atmosphere of N2, the reaction mixture was concentrated under reduced pressure. The resulting solid was partitioned between CH2Cl2 (500 mL) and H2O (500 mL). The layers were separated and the organic portion was concentrated under reduced pressure to give 40.5 g of 7-bromo-N-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-3-nitroquinolin-4-amine as a yellow, crystalline solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe resulting solid was partitioned between CH2Cl2 (500 mL) and H2O (500 mL)
  3. customThe layers were separated
  4. concentrationthe organic portion was concentrated under reduced pressure

Sources & evidence

ORD record
ord-513144b2d4ce473892066e6407a8eb9f
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

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