Boron tribromide → HCID 86639799, compound

HRID 1804836Notes

Reaction equation

HRID 1804836 reaction equation
[Cl:1][C:2]1[C:3]([C:27]([F:30])([F:29])[F:28])=[N:4][N:5]([CH2:8][C:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[C:21]([O:23]C)[C:20]([Cl:25])=[CH:19][C:18]=3[Cl:26])[CH2:13][CH2:12]2)=[O:10])[C:6]=1[CH3:7].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:27]([F:30])([F:29])[F:28])=[N:4][N:5]([CH2:8][C:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[C:21]([OH:23])[C:20]([Cl:25])=[CH:19][C:18]=3[Cl:26])[CH2:13][CH2:12]2)=[O:10])[C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 24863462HCID 24863462, compound

Product 1

HCID 86639799HCID 86639799, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-1-(1-(2,4-dichloro-5-methoxyphenyl)piperidin-4-yl)ethanone (100 mg, 0.206 mmol) in anhydrous DCM (1.5 mL) was cooled to −78° C. and then treated with boron tribromide (0.619 mL of a 1.0 M solution in heptanes, 0.619 mmol). The mixture was stirred for 30 min and the cooling bath was removed so that the reaction could warm to RT. After 3 h at RT, the reaction was poured unto crushed ice and extracted with DCM. The extract was dried (MgSO4) and concentrated on a rotary evaporator to give 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-1-(1-(2,4-dichloro-5-hydroxyphenyl)piperidin-4-yl)ethanone (80 mg, 0.170 mmol, 82% yield) as a pale yellow solid. LC-MS: 470.13, [M+H]; tR=2.10 min (method a).

Workup

  1. customthe cooling bath was removed so that the reaction
  2. waitAfter 3 h at RT
  3. additionthe reaction was poured
  4. customunto crushed ice
  5. extractionextracted with DCM
  6. dry with materialThe extract was dried (MgSO4)
  7. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-2c59799a1b25420ab86b138224364e2f
Source dataset
uspto-grants-2013_01
Patent number
US08354432B2

Reaction notes

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