tert-Butyldimethylsilyl trifluoromethanesulphonate → 8-(1-((tert-butyldimethylsilyl)oxy)vinyl)-3-methyl-N-(2-methyl-4-(methylsulfonyl)butan-2-yl)quinoxalin-2-amine

HRID 1056211Notes

Reaction equation

HRID 1056211 reaction equation
[CH3:1][C:2]1[C:11]([NH:12][C:13]([CH3:21])([CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH3:14])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:22](=[O:24])[CH3:23])[N:3]=1.FC(F)(F)S(O[Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])(=O)=O>C(Cl)Cl>[Si:31]([O:24][C:22]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[N:10]=[C:11]([NH:12][C:13]([CH3:21])([CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH3:14])[C:2]([CH3:1])=[N:3]2)=[CH2:23])([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 897821841-(2-Methyl-3-((2-methyl-4-(methylsulfonyl)butan-2-yl)amino)quinoxalin-5-yl)ethanone

Product 1

HCID 897821258-(1-((tert-butyldimethylsilyl)oxy)vinyl)-3-methyl-N-(2-methyl-4-(methylsulfonyl)butan-2-yl)quinoxalin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(2-methyl-3-((2-methyl-4-(methylsulfonyl)butan-2-yl)amino)quinoxalin-5-yl)ethanone (338c, 0.51 g, 1.46 mmol), tert-butyldimethylsilyl trifluoromethanesulfonate (0.50 mL, 2.20 mmol), and TEA (0.61 mL, 4.40 mmol) in DCM (14.68 mL) was stirred at 0° C. for 30 min when silyl enol ether was observed via lcms. The reaction mixture was diluted with DCM (150 mL), added to a separatory funnel, and washed with saturated aq. NaHCO3 (75 mL) before the organic layer was separated, dried over Na2SO4, and concentrated to give 8-(1-((tert-butyldimethylsilyl)oxy)vinyl)-3-methyl-N-(2-methyl-4-(methylsulfonyl)butan-2-yl)quinoxalin-2-amine (338d) as a yellow oil. MS (ESI, pos. ion) m/z: 464.2 (M+1).

Workup

  1. additionadded to a separatory funnel
  2. washwashed with saturated aq. NaHCO3 (75 mL) before the organic layer
  3. customwas separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-60d80d6d319d4562a65ae3484a8962e2
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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