Chlorotrimethylsilane → Tert-butyl [quinolin-8-yl(toluene-4-sulfonyl)methyl]carbamate

HRID 1170388Notes

Reaction equation

HRID 1170388 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH:11]=O)[CH:4]=[CH:3][CH:2]=1.[C:13](=[O:20])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[NH2:14].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([O-])(=[O:29])=[O:28])=[CH:23][CH:22]=1.[Na+].Cl[Si](C)(C)C>C(#N)C.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH:11]([NH:14][C:13](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[S:27]([C:24]2[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=2)(=[O:29])=[O:28])[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 77922tert-Butyl carbamateHCID 1701038-QuinolinecarboxaldehydeHCID 3720192Sodium 4-methylbenzenesulfonate

Product 1

HCID 86621950Tert-butyl [quinolin-8-yl(toluene-4-sulfonyl)methyl]carbamateYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

5.0 g (32 mmol) of 8-quinolinecarbaldehyde were added to a solution of 5.6 g (48 mmol) of tert-butyl carbamate and 8.5 g (48 mmol) of sodium p-toluenesulfonate in 112 ml of acetonitrile under argon. While cooling to 0-10° C., 6.9 g (64 mmol) of chlorotrimethylsilane were added dropwise, and the mixture was left to stir at room temperature overnight. After addition of 130 ml of water, the precipitated product was filtered off with suction and dried in vacuo at 50° C. 11.4 g of tert-butyl [quinolin-8-yl(toluene-4-sulfonyl)methyl]carbamate were obtained.

Workup

  1. waitthe mixture was left
  2. filtrationthe precipitated product was filtered off with suction
  3. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-ef7c726258f041f19336c72f5bc1d5e2
Source dataset
uspto-grants-2010_11
Patent number
US07825264B2

Reaction notes

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