Boron tribromide → HCID 57970104, compound

HRID 1666621Notes

Reaction equation

HRID 1666621 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([N:14]3[CH2:18][CH2:17][C@H:16]([NH:19][C:20]4[CH:29]=[C:28]([CH3:30])[C:27]5[C:22](=[CH:23][CH:24]=[C:25]([O:31]C)[CH:26]=5)[N:21]=4)[CH2:15]3)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[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]2([C:12]([N:14]3[CH2:18][CH2:17][C@H:16]([NH:19][C:20]4[CH:29]=[C:28]([CH3:30])[C:27]5[C:22](=[CH:23][CH:24]=[C:25]([OH:31])[CH:26]=5)[N:21]=4)[CH2:15]3)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57970077HCID 57970077, compound

Product 1

HCID 57970104HCID 57970104, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (S)-(1-(4-chlorophenyl)cyclobutyl)-(3-(6-methoxy-4-methylquinolin-2-ylamino)pyrrolidin-1-yl)methanone (0.60 g) in dichloromethane (50 mL) was cooled to −78° C., followed by addition of a solution of 1 M boron tribromide in dichloromethane (7.3 mL), and the mixture was stirred for 12 h while slowly heating to room temperature. To the reaction mixture was added a saturated sodium hydrogencarbonate solution to make it basic, and 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 and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (silica gel, chloroform/methanol, and NH silica gel, chloroform/methanol) and crystallized with ethyl acetate to obtain white solid (S)-(1-(4-chlorophenyl)cyclobutyl)-(3-(6-hydroxy-4-methylquinolin-2-ylamino)pyrrolidin-1-yl)methanone (0.278 g).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. concentrationconcentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (silica gel, chloroform/methanol, and NH silica gel, chloroform/methanol)
  4. customcrystallized with ethyl acetate

Sources & evidence

ORD record
ord-680332b00a0740d599b68ba1f218f60e
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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