Ethyl Bromide → HCID 90312660, compound

HRID 1524152Notes

Reaction equation

HRID 1524152 reaction equation
[C:1](=O)([S:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[C:15]([F:17])[C:14]([C:18]2[CH:23]=[N:22][C:21]([NH2:24])=[CH:20][N:19]=2)=[CH:13][CH:12]=1)[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+].BrCC>CO>[CH2:1]([S:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[CH:13][C:14]([C:18]2[N:19]=[CH:20][C:21]([NH2:24])=[N:22][CH:23]=2)=[C:15]([F:17])[CH:16]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 131733122HCID 131733122, compound

Product 1

HCID 90312660HCID 90312660, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of S-(4′-(5-aminopyrazin-2-yl)-5′-fluorobiphenyl-2-yl)methyl ethanethioate (100 mg, 0.280 mmol) in CH3OH (30 mL) were added Ph3P (150 mg, 0.560 mmol), K2CO3 (78 mg, 0.56 mmol), and bromoethane [drop-wise addition (60 mg, 0.56 mmol)] at rt. The reaction mixture was stirred at rt for 16 h, before removing the solvent in vacuo. The crude product was purified first by preparative-TLC followed by HPLC to give the title compound (70 mg HCOOH salt, 73%).

Workup

  1. custombefore removing the solvent in vacuo
  2. customThe crude product was purified first

Sources & evidence

ORD record
ord-561a990042fb40b3ad3f2b2410ddaf4e
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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