Hydrochloric Acid → HCID 136352413, compound

HRID 1835327Notes

Reaction equation

HRID 1835327 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:6][N:7]([CH3:31])[C:8](=[O:30])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28]C)=[N:11][CH:10]=1.B(Br)(Br)Br.Cl.[OH-].[Na+]>ClCCl.O>[F:39][C:2]([F:1])([F:40])[C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[CH2:6][N:7]([CH3:31])[C:8](=[O:30])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[OH:28])=[N:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 23502787HCID 23502787, compound

Product 1

HCID 136352413HCID 136352413, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 80 mg (0.14 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-(2-methoxy-phenyl)-N-methyl-4-o-tolyl-nicotinamide in 1.5 ml dichloromethane 0.17 ml of a 1M solution of boron tribromide in dichloromethane (0.17 mmol) were added dropwise at 0° C. The temperature was allowed to warm to room temperature over night. Water and a 1M aqueous solution of hydrochloric acid were added. After 5 min the mixture was neutralized by addition of 1M aqueous sodium hydroxide solution and extracted with dichloromethane. The organic layer was dried with sodium sulfate and concentrated. Column chromatography afforded 67 mg (86%) of the title compound as a white solid.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5d885737930e49559624225a7b7e56ea
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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