Boron tribromide → HCID 57941176, compound

HRID 1437451Notes

Reaction equation

HRID 1437451 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:10][CH2:11][N:12](C(OCC2C=CC=CC=2)=O)[CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH:14]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:10][CH2:11][NH:12][CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69017489HCID 69017489, compound

Product 1

HCID 57941176HCID 57941176, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a flask equipped with stir bar was added benzyl 4-(2,5-difluorophenyl)-6-(3-methoxyphenyl)-3,6-dihydropyridine-1(2H)-carboxylate (1-4, 0.51 g, 1.17 mmol) and dichloromethane (20 mL). The resulting solution was cooled to 0° C. and treated with BBr3 (0.15 mL, 1.17 mmol). The reaction was stirred at 0° C. for 4 h, then warmed to 23° C. Upon completion, the reaction was diluted with dichloromethane (100 mL) and washed with water (3×100 mL). The organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was carried into the subsequent acylation.

Workup

  1. customTo a flask equipped
  2. stirringThe reaction was stirred at 0° C. for 4 h
  3. temperaturewarmed to 23° C
  4. washwashed with water (3×100 mL)
  5. dry with materialThe organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb3f8cff3cbb495bb7b5536eef140e69
Source dataset
uspto-grants-2009_11
Patent number
US07622489B2

Reaction notes

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