Boron tribromide → HCID 136413215, compound

HRID 470621Notes

Reaction equation

HRID 470621 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]([CH:29]([CH3:31])[CH3:30])[CH2:25][CH2:24]3)[N:18]=2)[CH:10]=[CH:11][C:12]=1[O:13]C>ClCCl.N>[CH:29]([N:26]1[CH2:27][CH2:28][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)[CH2:24][CH2:25]1)([CH3:31])[CH3:30]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 67397310HCID 67397310, compound2×

Product 1

HCID 136413215HCID 136413215, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (0.229 mL, 2.42 mmol) was added dropwise to a cooled solution of 4-{5-[2-(3,4-Dimethoxy-phenyl)-vinyl]-[1,2,4]oxadiazol-3-ylmethyl}-1-isopropyl-piperidine (compound of Example 21; 0.15 g, 0.4 mmol) in dichloromethane (5 mL) at −78° C. The reaction mixture was warmed to room temperature and stirred for 6 h. The reaction mixture 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 mixture 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-20e8ec680c2747ffa8dfd12545444f56
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Reaction notes

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