Water → HCID 58675237, compound

HRID 2179719Notes

Reaction equation

HRID 2179719 reaction equation
B(Br)(Br)Br.Cl.[N:6]12[CH2:13][CH2:12][CH:9]([CH2:10][CH2:11]1)[C@@H:8]([NH:14][C:15]([C:17]1S[C:19]3[C:25]([C:26]4C=C([CH:32]=[CH:33][CH:34]=4)C(O)=O)=[CH:24][CH:23]=[CH:22][C:20]=3[CH:21]=1)=O)[CH2:7]2.C([O:37][CH2:38][CH3:39])C.[OH-:40].[Na+].[OH2:42]>ClCCl>[N:6]12[CH2:13][CH2:12][CH:9]([CH2:10][CH2:11]1)[C@@H:8]([NH:14][C:15]([C:17]1[O:42][C:19]3[C:25]([C:26]4[CH:34]=[CH:33][CH:32]=[CH:39][C:38]=4[OH:37])=[CH:24][CH:23]=[CH:22][C:20]=3[CH:21]=1)=[O:40])[CH2:7]2

Participants

7

Reactant 5

HCID 962WaterHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 67314106HCID 67314106, compound

Product 1

HCID 58675237HCID 58675237, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.42 ml of a 1 M boron tribromide solution in dichloromethane are added dropwise to a suspension, cooled to −20° C., of 200 mg (0:48 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-(2-methoxyphenyl)-1-benzofuran-2-carboxamide hydrochloride (Example 102) in 8 ml of dichloromethane. After 2 h, the reaction is stopped by adding diethyl ether. The mixture is stirred at room temperature for 30 min and, after addition of water, neutralized with 1N sodium hydroxide solution. After extraction with ethyl acetate, the organic phases are combined and dried over sodium sulphate. Concentration and drying under high vacuum result in 125.9 mg (71.7% of theory) of the title compound.

Workup

  1. extractionAfter extraction with ethyl acetate
  2. dry with materialdried over sodium sulphate
  3. concentrationConcentration
  4. customdrying under high vacuum

Sources & evidence

ORD record
ord-bdeebd3dd4fc44e392fc72ecd3360b23
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Reaction notes

Loading…