Water → HCID 86703921, compound

HRID 1049920Notes

Reaction equation

HRID 1049920 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH2:5].[N:10]1[C:15]([CH3:16])=CC=C[C:11]=1[CH3:17].Cl[CH2:19][CH2:20][S:21](Cl)(=[O:23])=[O:22].[OH2:25]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][S:21]([CH2:20][CH2:19][N:10]2[CH2:11][CH2:17][O:25][CH2:16][CH2:15]2)(=[O:23])=[O:22])[CH:6]=[C:7]([F:9])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 150201553-Bromo-5-fluoroaniline

Product 1

HCID 86703921HCID 86703921, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-bromo-5-fluoroaniline (CAS 134168-97-1) (1.0 g, 5.3 mmol) and 2,6-lutidine (2.8 g, 26.5 mmol) in anhydrous DCM (30 mL), was added dropwise 2-chloro-ethanesulfonyl chloride (CAS 1622-32-8) (1.0 g, 6.3 mmol) in DCM (5 mL) at r.t. The mixture was stirred at r.t. for 30 min, and compound 34-A (1.5 g, 16 mmol) was added and stirred for 1 h. Water (50 mL) was added, and the mixture was extracted with EtOAc (100 mL×2). The combined organic layers was washed with sat NaCl (50 mL), dried over Na2SO4, concentrated, and purified by column to give the product (700 mg, yield 37%).

Workup

  1. stirringstirred for 1 h
  2. extractionthe mixture was extracted with EtOAc (100 mL×2)
  3. washThe combined organic layers was washed with sat NaCl (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by column

Sources & evidence

ORD record
ord-f417d11e7b8147ec9e173d0f4e491f15
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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