Boron tribromide → HCID 136413216, compound

HRID 470623Notes

Reaction equation

HRID 470623 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][C:17]2[O:21][N:20]=[C:19]([CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])[CH2:25][CH2:24]3)[N:18]=2)[CH:10]=[CH:11][C:12]=1[O:13]C>ClCCl.N>[CH3:33][N:31]([CH3:32])[CH2:30][CH2:29][N:26]1[CH2:25][CH2:24][CH:23]([CH2:22][C:19]2[N:18]=[C:17]([CH:16]=[CH:15][C:9]3[CH:8]=[C:7]([OH:6])[C:12]([OH:13])=[CH:11][CH:10]=3)[O:21][N:20]=2)[CH2:28][CH2:27]1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 67395701HCID 67395701, compound2×

Product 1

HCID 136413216HCID 136413216, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (0.14 mL, 1.49 mmol) was added dropwise to a cooled solution of [2-(4-{5-[2-(3,4-dimethoxy-phenyl)-vinyl]-[1,2,4]oxadiazol-3-ylmethyl}-piperidin-1-yl)-ethyl]-dimethyl-amine (compound of Example 23; 0.10 g, 0.25 mmol) in dichloromethane (5 mL) at −78° C. The reaction mixture was warmed to room temperature and stirred for 6 h. The reaction mass was quenched with methanol (2 mL) and the organic solvent was evaporated. The residue obtained was dissolved in 8% methanolic ammonia (5 mL) and the inorganic solid obtained was removed by filtration. The filtrate was concentrated and purified by column chromatography (silica gel, 3% methanol in chloroform) to afford the title compound.

Workup

  1. customThe reaction mass was quenched with methanol (2 mL)
  2. customthe organic solvent was evaporated
  3. customThe residue obtained
  4. customthe inorganic solid obtained
  5. customwas removed by filtration
  6. concentrationThe filtrate was concentrated
  7. custompurified by column chromatography (silica gel, 3% methanol in chloroform)

Sources & evidence

ORD record
ord-ae4192ddd75f40dfbe85c5ca675cf90d
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Reaction notes

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