Benzyl Bromide → HCID 86606713, compound

HRID 1012849Notes

Reaction equation

HRID 1012849 reaction equation
[CH2:1]([Br:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[N:16]12[CH2:23][CH2:22][CH:19]([CH2:20][CH2:21]1)[C@@H:18]([NH:24][C:25]([C:27]1[O:28][C:29]3[C:35]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[O:42][CH3:43])=[CH:34][CH:33]=[CH:32][C:30]=3[CH:31]=1)=[O:26])[CH2:17]2>CN(C=O)C>[Br-:8].[CH2:1]([N+:16]12[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23]1)[C@@H:18]([NH:24][C:25]([C:27]1[O:28][C:29]3[C:35]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[O:42][CH3:43])=[CH:34][CH:33]=[CH:32][C:30]=3[CH:31]=1)=[O:26])[CH2:17]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67312922HCID 67312922, compound

Product 1

HCID 86606713HCID 86606713, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

288 μl (2.42 mmol) of benzyl bromide and 502 mg (3.63 mmol) of potassium carbonate are added to a solution of 500 mg (1.21 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-(2-methoxyphenyl)-1-benzofuran-2-carboxamide hydrochloride (Example 102) in 12.5 ml of DMF. After 20 h at 50° C., the reaction mixture is purified by preparative HPLC. The product fractions are concentrated and, after addition of 50% strength hydrobromic acid, again concentrated and dried under high vacuum. Recrystallization from cyclohexane/acetone affords 537 mg (77% of theory) of the title compound.

Workup

  1. customthe reaction mixture is purified by preparative HPLC
  2. concentrationThe product fractions are concentrated
  3. additionafter addition of 50% strength hydrobromic acid
  4. concentrationagain concentrated
  5. customdried under high vacuum
  6. customRecrystallization from cyclohexane/acetone

Sources & evidence

ORD record
ord-1b9ab4c5332e4d87b5d175b4604df591
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

Loading…