Tert-Butylamine → HCID 89782204, compound

HRID 1056048Notes

Reaction equation

HRID 1056048 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5](Cl)[C:6]([C:12]([F:15])([F:14])[F:13])=[N:7]2.[CH3:17][C:18]([NH2:21])([CH3:20])[CH3:19]>CS(C)=O.C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([NH:21][C:18]([CH3:20])([CH3:19])[CH3:17])[C:6]([C:12]([F:15])([F:14])[F:13])=[N:7]2

Participants

5

Reactant 2

HCID 6385Tert-Butylamine2×HCID 89782123HCID 89782123, compound

Product 1

HCID 89782204HCID 89782204, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-bromo-3-chloro-2-(trifluoromethyl)quinoxaline (239 mg, 0.767 mmol) and 2-methylpropan-2-amine (243 μl, 2.302 mmol; Aldrich) in DMSO (7.6 ml) was stirred at 100° C. for 7 h (more 2-methylpropan-2-amine (243 μl, 2.302 mmol) was added after 3 h). The mixture was then diluted with DCM (150 ml), added to a separatory funnel, and washed with saturated aq. NaHCO3 (2×100 ml) before the organic layer was separated, dried over Na2SO4, and concentrated. Purification by silica gel (100% hexanes to 20% EtOAc in hexanes) provided 8-bromo-N-(tert-butyl)-3-(trifluoromethyl)quinoxalin-2-amine (224d, 77% yield) as a light yellow solid. MS (ESI, pos. ion) m/z: 348.0/350.2 (M+1).

Workup

  1. additionwas added after 3 h)
  2. additionadded to a separatory funnel
  3. washwashed with saturated aq. NaHCO3 (2×100 ml) before the organic layer
  4. customwas separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by silica gel (100% hexanes to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7aac08f9c0cf4ef9b1ff393b3d4b2e84
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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