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1,2-Dibromoethane → HCID 59632449, compound

HRID 2369062
Notes
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Reaction equation

HRID 2369062 reaction equation
Br[CH2:2][CH2:3]Br.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[C:16]([C:17]2[S:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:23]=3)=[CH:20][CH:21]=2)=[CH:15][C:14]([CH2:32][C:33]#[N:34])=[N:13]1.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[C:16]([C:17]2[S:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([S:28]([CH3:31])(=[O:29])=[O:30])[CH:23]=3)=[CH:20][CH:21]=2)=[CH:15][C:14]([C:32]2([C:33]#[N:34])[CH2:3][CH2:2]2)=[N:13]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 59633179HCID 59633179, compound

Product 1

HCID 59632449HCID 59632449, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalyst
HCID 962
Water
Solvent

Procedure

1,2-dibromoethane (40 μL, 0.46 mmol) was added to a stirred suspension of the [1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]acetonitrile (68 mg, 0.15 mmol), benzyltriethylammonium chloride (20 mg, 0.088 mmol), and 50% aqueous NaOH (2 mL) at 0° C., the resulting mixture was stirred at rt overnight. After diluted with water, the mixture was extracted with ether. The combined extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (0-70% EtOAc/hexanes) to give the title compound as a white solid (59 mg, 82%). 1HNMR (CDCl3): δ 8.04 (m, 1H), 7.84-7.82 (m, 1H), 7.74-7.71 (m, 1H), 7.58-7.43 (m, 5H), 7.21 (d, 1H), 6.79-6.77 (m, 2H), 3.07 9d, 3H), 1.73-1.68 (m, 4H). MS(ES): 480 [M+H]+.

Workup

  1. extractionthe mixture was extracted with ether
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography (0-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9b1d2b0fe3904cff8200b408e381d2b6
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08703805B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes