Boron tribromide → HCID 87364811, compound

HRID 2038463Notes

Reaction equation

HRID 2038463 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16]C)[CH2:6]1)=[O:4].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:19][C:2]([F:1])([F:18])[C:3]([N:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 584046022,2,2-Trifluoro-1-[3-(2-methoxyphenyl)pyrrolidin-1-yl]ethan-1-one

Product 1

HCID 87364811HCID 87364811, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the title compound of Example 43 Step A (1.2 g, 4.4 mmol) in CH2Cl2 (15 mL) at 0° C. was added BBr3 (1 M in CH2Cl2, 9.8 mL, 9.8 mmol). After warming to rt and allowing to stir for 18 h, sat'd NaHCO3 (aq.) was added slowly. The reaction was then extracted with CH2Cl2. The combined organic layers were dried and used in the next step without further purification. MS (ESI): mass calcd. for C12H12F3NO2, 259.2; m/z found, 260.1 [M+H]+. 1H NMR (CDCl3): 7.22-7.11 (m, 2H), 6.97-6.88 (m, 1H), 6.87-6.77 (m, 1H), 4.26-4.14 (m, 1H), 4.04-3.94 (m, 0.5H), 3.93-3.84 (m, 0.5H), 3.82-3.71 (m, 1H), 3.70-3.53 (m, 2H), 2.44-2.26 (m, 1.5H), 2.25-2.13 (m, 0.5H).

Workup

  1. extractionThe reaction was then extracted with CH2Cl2
  2. customThe combined organic layers were dried
  3. customused in the next step without further purification

Sources & evidence

ORD record
ord-2fe181753c104fabb73a096fea2d6b83
Source dataset
uspto-grants-2013_11
Patent number
US08575364B2

Reaction notes

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