Dichloromethane → HCID 58765153, compound

HRID 860726Notes

Reaction equation

HRID 860726 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[C:6]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:5]1[C:23]1[N:24]([CH2:30][CH2:31]Br)[C:25]([Br:29])=[C:26]([Br:28])[N:27]=1)[CH:2]=[CH2:3].C(Cl)Cl>C[O-].[Na+]>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[C:6]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:5]1[C:23]1[N:24]([CH:30]=[CH2:31])[C:25]([Br:29])=[C:26]([Br:28])[N:27]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 58765155HCID 58765155, compound

Product 1

HCID 58765153HCID 58765153, compound

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
65 °C

Procedure

Methyl 1-allyl-3-cyclohexyl-2-(4,5-dibromo-1-(2-bromoethyl)-1H-imidazol-2-yl)-1H-indole-6-carboxylate was dissolved in a solution of sodium methoxide (0.5 M in Methanol from Aldrich, 10 mL) and the light yellow solution was heated to 65° C. for 1h. Methylene chloride (20 mL) was then added, followed by ice-water (50 mL). The aqueous layer was then adjusted to pH 5, and the organic layer was separated, dried (Na2SO4), filtered and evaporated to give the title compound in a form pure enough for use in the next step. 1H NMR (500 MHz, CDCl3) δ 0.8–1.90 (m, 10 H), 2.50 (m, 1H), 3.92 (s, 3H), 4.55 (dd, 1H, J=4.5, 16.5 Hz), 4.70 (dd, 1H, J=6.5, 16.5 Hz), 5.85 (dd, 1H, J=6.0, 17.5 Hz), 5.05 (d, 1H, J=10.5 Hz), 5.09 (d, 1H, J=9.0 Hz), 5.26 (d, 1H, J=13.5 Hz), 5.7–5.80 (m, 1H), 6.56 (dd, 1H, J=9.0, 16.0 Hz), 7.77 (d, 1H, J=8.0 Hz), 7.82 (d, 1H, J=8.0 Hz), 8.07 (s, 1H).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-5822047cf6344da68d5495b71c48aa4e
Source dataset
uspto-grants-2006_12
Patent number
US07153848B2

Reaction notes

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