Boron tribromide → HCID 57970109, compound

HRID 1666624Notes

Reaction equation

HRID 1666624 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:30])[C:9]([N:11]2[CH2:15][CH2:14][C@H:13]([NH:16][C:17]3[CH:26]=[C:25]([CH3:27])[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([O:28]C)[CH:23]=4)[N:18]=3)[CH2:12]2)=[O:10])=[CH:4][CH:3]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:30])[C:9]([N:11]2[CH2:15][CH2:14][C@H:13]([NH:16][C:17]3[CH:26]=[C:25]([CH3:27])[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([OH:28])[CH:23]=4)[N:18]=3)[CH2:12]2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57970113HCID 57970113, compound

Product 1

HCID 57970109HCID 57970109, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (S)-1-(4-chlorophenyl)-2-(3-(6-methoxy-4-methylquinolin-2-ylamino)pyrrolidin-1-yl)ethane-1,2-dione (0.467 g) in dichloromethane (50 mL) was cooled to −78° C., followed by addition of a solution (6.1 mL) of 1 M boron tribromide in dichloromethane, and the mixture was stirred for 3 h while heating slowly to room temperature. To the reaction mixture was added a saturated sodium hydrogencarbonate solution to make it basic, and then the mixture was extracted with chloroform. The aqueous layer was reextracted with a mixed solution of ethyl acetate and n-butanol, then the organic layer was combined, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (silica gel, chloroform/methanol, and NH silica gel, chloroform/methanol) to obtain light yellow amorphous (S)-1-(4-chlorophenyl)-2-(3-(6-hydroxy-4-methylquinolin-2-ylamino)pyrrolidin-1-yl)ethane-1,2-dione (0.068 g).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (silica gel, chloroform/methanol, and NH silica gel, chloroform/methanol)

Sources & evidence

ORD record
ord-7c560f97ef2242da8b00ae73d3aedb0b
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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