Boron tribromide → HCID 59764871, compound

HRID 406479Notes

Reaction equation

HRID 406479 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[Cl:33])[C:5]([NH:7][CH2:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28]C)[CH2:18][CH2:17]2)[CH2:12]1)=[O:10])=[O:6].B(Br)(Br)Br>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[Cl:33])[C:5]([NH:7][CH2:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[OH:28])[CH2:18][CH2:17]2)[CH2:12]1)=[O:10])=[O:6]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 59764766HCID 59764766, compound

Product 1

HCID 59764871HCID 59764871, compoundYield 85.9%

Procedure

3,4-Dichloro-N-(2-(3-(4-(2-methoxyphenyl)piperidin-1-yl)pyrrolidin-1-yl)-2-oxoethyl)benzamide (0.035 g, 0.071 mmol) and boron tribromide (1M solution in DCM, 0.357 mL, 0.357 mmol) was stirred at about 0° C. for about 1 hour. The precipitate was collected by filtration, rinsed with DCM. The residue was purified by preparative RP-HPLC (15% acetonitrile/0.05M aqueous ammonium acetate buffered to pH 4.5 for 3 min then 15% to 60% acetonitrile/0.05M aqueous ammonium acetate buffered to pH 4.5 over 6 min at 25 mL/min; APCI positive mode detection; Xterra prep. MS C18 19×50 mm column) to yield 3,4-dichloro-N-(2-(3-(4-(2-hydroxyphenyl)piperidin-1-yl)pyrrolidin-1-yl)-2-oxoethyl)benzamide (0.029 g, 0.061 mmol). RP-HPLC (Table 1, Method a) Rt 1.91 min; m/z: (M+H)+ 476.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washrinsed with DCM
  3. customThe residue was purified by preparative RP-HPLC (15% acetonitrile/0.05M aqueous ammonium acetate
  4. wait15% to 60% acetonitrile/0.05M aqueous ammonium acetate buffered to pH 4.5 over 6 min at 25 mL/min

Sources & evidence

ORD record
ord-a0183a722b3549a18b36ee01cafdaf34
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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