1,2-Dibromoethane → HCID 57443269, compound

HRID 2261750Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][CH3:23])=[C:18]([CH3:24])[CH:17]=2)=[C:12]([CH:25]([CH3:27])[CH3:26])[CH:11]=[N:10]1.C(N(CC)CC)C.CCOC(C)=O.[Br:41][CH2:42][CH2:43]Br>>[Br:41][CH2:42][CH2:43][N:22]([C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][C:13]2[N:9]([C:3]3[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[N:10]=[CH:11][C:12]=2[CH:25]([CH3:27])[CH3:26])=[CH:17][C:18]=1[CH3:24])[CH3:23]

Participants

Reactant 4

HCID 78391,2-Dibromoethane

HCID 8471Triethylamine

HCID 8857Ethyl Acetate

HCID 67527941HCID 67527941, compound

Product 1

HCID 57443269HCID 57443269, compoundYield 37%

Conditions

Temperature: 90 °C

Procedure

To an ambient temperature solution of {4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-methyl-amine (1.12 g, 2.77 mmol) in 1,2-dibromoethane (5 mL) is added triethylamine (1.54 mL, 11.08 mmol). The reaction is heated to 90° C. overnight. EtOAc is added to the reaction mixture. The resultant mixture is washed with brine, dried (MgSO4), and chromatographed (0% to 20% EtOAc/Hex) to yield the title compound (520 mg, 37%). 1H NMR (400 MHz, CDCl3) δ 7.70 (s, 1H), 7.43-7.40 (m, 2H), 7.31 (dd, 1H, J=9.0, 7.1 Hz), 6.93 (d, 1H, J=7.3 Hz), 6.61-6.54 (m, 2H), 4.77 (s, 2H), 3.34 (t, 2H, J=6.5 Hz), 3.26 (t, 2H, J=6.7 Hz), 2.99 (sept, 1H, J=7.0 Hz), 2.65 (s, 3H), 2.26 (s, 3H), 1.30 (d, 6H, J=7.0 Hz).

Workup

washThe resultant mixture is washed with brine
dry with materialdried (MgSO4)
customchromatographed (0% to 20% EtOAc/Hex)

Sources & evidence

ORD record: ord-f45bb6bf51ff43dd871a97a8e27166f2
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846960B2

Reaction notes

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