Diethyl Ether → HCID 58675237, compound

HRID 1012847Notes

Reaction equation

HRID 1012847 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]1[O:18][C:19]3[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32]C)=[CH:24][CH:23]=[CH:22][C:20]=3[CH:21]=1)=[O:16])[CH2:7]2.C(OCC)C.[OH-].[Na+]>ClCCl.O>[N:6]12[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13]1)[C@@H:8]([NH:14][C:15]([C:17]1[O:18][C:19]3[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[OH:32])=[CH:24][CH:23]=[CH:22][C:20]=3[CH:21]=1)=[O:16])[CH2:7]2

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 67312922HCID 67312922, compound

Product 1

HCID 58675237HCID 58675237, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2.42 ml of a 1 M boron tribromide solution in dichloromethane are added dropwise to a suspenion, 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-63576cd6dce942d3b48b1b4b9ea395a6
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

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