Boron tribromide → HCID 136387753, compound

HRID 2283634Notes

Reaction equation

HRID 2283634 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[CH:14]=1.B(Br)(Br)Br>ClCCl>[NH2:19][C:15]1[CH:14]=[C:13]([C:4]2[CH:5]=[C:6]([C:9]([F:11])([F:10])[F:12])[CH:7]=[CH:8][C:3]=2[OH:2])[CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66652889HCID 66652889, compound

Product 1

HCID 136387753HCID 136387753, compoundYield 52,319.398%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-[2-methoxy-5-(trifluoromethyl)phenyl]pyridin-2-amine (Preparation 16, 2.8 g, 0.01 mmol) in dichloromethane (5 mL) at 0° C. was added drop-wise a 1.0 M solution of boron tribromide in dichloromethane (31.3 mL, 31.3 mmol). After stirring for 20 hours at ambient temperature, the reaction mixture was quenched with water and saturated aqueous sodium bicarbonate until basic. The aqueous phase was extracted with 15% isopropyl alcohol in chloroform (×3). The combined organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (0% to 10% methanol in chloroform gradient elution) and concentrated in vacuo to afford the title compound as a yellow solid (1.33 g).

Workup

  1. customthe reaction mixture was quenched with water and saturated aqueous sodium bicarbonate until basic
  2. extractionThe aqueous phase was extracted with 15% isopropyl alcohol in chloroform (×3)
  3. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (0% to 10% methanol in chloroform gradient elution)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb460d3008ac44bc9b7b44836d8a5193
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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