Carbon tetrabromide → HCID 86700445, compound

HRID 879634Notes

Reaction equation

HRID 879634 reaction equation
C([Li])CCC.[CH:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[S:19][CH:18]=[N:17][CH:16]=2)[CH2:11][CH2:10]1)([CH3:8])[CH3:7].C(Br)(Br)(Br)[Br:21]>C1COCC1>[Br:21][C:18]1[S:19][C:15]([N:12]2[CH2:11][CH2:10][N:9]([CH:6]([CH3:8])[CH3:7])[CH2:14][CH2:13]2)=[CH:16][N:17]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 86700444HCID 86700444, compoundHCID 178418339Butyllithium

Product 1

HCID 86700445HCID 86700445, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

At −78° C., n-butyl lithium (2.5 N in hexane, 0.27 mL, 2 eq.) was added to 5-(4-isopropylpiperazin-1-yl)thiazole (28 mg, 0.132 mmol) in 1 mL THF. CBr4 (22 mg, 0.5 eq.) was added after 30 minutes. The reaction was stirred at −78° C. for 2 hours. The reaction was quenched by adding water. The reaction crude was extracted using EtOAc. The organic layers were concentrated and purified via Combiflash (0-20% MeOH in EtOAc) to give desired product. LCMS-ESI+: calc'd for C10H17BrN3S: 290.0 (M+H+); Found: 290.1 (M+H+).

Workup

  1. customThe reaction was quenched
  2. additionby adding water
  3. customThe reaction crude
  4. extractionwas extracted
  5. concentrationThe organic layers were concentrated
  6. custompurified via Combiflash (0-20% MeOH in EtOAc)

Sources & evidence

ORD record
ord-04c8041f87304b8090356b0afeb30615
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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