Carbon tetrabromide → HCID 68840477, compound

HRID 1432727Notes

Reaction equation

[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][CH:20]=[N:19][C:18]=3[C:22]([F:25])([F:24])[F:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[Li]CCCC.C(Br)(Br)(Br)[Br:32]>C1COCC1>[Br:32][C:20]1[S:21][C:17]([C:13]2[N:8]3[N:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:7]3=[N:15][C:14]=2[CH3:16])=[C:18]([C:22]([F:23])([F:24])[F:25])[N:19]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 8-(1-ethyl-propyl)-2,6-dimethyl-3-(4-trifluoromethyl-thiazol-5-yl)-imidazo[1,2-b]pyridazine (915 mg, 2.48 mmol) in 40 mL of THF under N2 atmosphere al −78° C., BuLi (1.86 mL 1.6 M in hexane, 2.98 mmol) is slowly added. The mixture is stirred at −78° C. for 30 minutes. Then, a solution of CBr4 (989 mg, 2.98 mmol) in 3 mL of THF is added, and the mixture is stirred at −78° C. for 45 minutes. The reaction is quenched by addition of NH4Cl saturated solution (50 mL), extracted with Et2O (2×50 mL), dried over MgSO4, and concentrated in vacuo. Crude product is purified by flash chromatography on silica gel (eluent CH2Cl2) to obtain 685 mg of the title compound (Yield: 62%). 1H NMR (CDCl3): δ0.86 (t, J=7.5 Hz, 6H), 1.82 (m, 4H), 2.45 (s, 3H), 2.51 (s, 3H), 3.27 (m, 1H), 6.74 (s, 1H). ESIMS: m/z 447, 449 [M+H]+.

Workup

stirringthe mixture is stirred at −78° C. for 45 minutes
customThe reaction is quenched by addition of NH4Cl saturated solution (50 mL)
extractionextracted with Et2O (2×50 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customCrude product is purified by flash chromatography on silica gel (eluent CH2Cl2)

Sources & evidence

ORD record: ord-f5788cd7b55b4cc094089ebf95962adc
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612067B2

Reaction notes

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