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2,3-Dibromobutane → HCID 59632583, compound

HRID 2369051
Notes
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Reaction equation

HRID 2369051 reaction equation
[Mg].Br[CH:3]([CH3:7])[CH:4](Br)[CH3:5].C[O:9][C:10]([C:12]1[CH:16]=[C:15]([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)[N:14]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[Cl:38])[N:13]=1)=O.[NH4+].[Cl-]>C1COCC1>[Cl:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[N:14]1[C:15]([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:16][C:12]([C:10]2([OH:9])[CH2:5][CH2:4][CH2:3][CH2:7]2)=[N:13]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 215082,3-DibromobutaneHCID 25517Ammonium ChlorideHCID 5462224Magnesium2×HCID 59631939HCID 59631939, compound

Product 1

HCID 59632583HCID 59632583, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

Magnesium turnings (300 mg, 12.5 mmol) was introduced into a oven-dried flask under N2, covered with anhydrous THF (150 mL), and a solution of dibromobutane (0.72 mL, 6.08 mmol) in anhydrous THF (20 mL) was added dropwise at ambient temperature at such a rate that the temperature of the reaction mixture did not rise above 40° C. The mixture was stirred at ambient temperature for 1 h, and the magnesium turnings disappeared. 1-(2-chloro-phenyl)-5-[5-(3-methanesulfonyl-phenyl)thiophen-2-yl]-1H-pyrazole-3-carboxylic acid methyl ester (2.37 g, 5 mmol) was added as a solid, and the resulting dark-purple solution was stirred at room temperature under N2 for 1 h, At 0° C. aqueous NH4Cl solution was added, and then extracted with EtOAc, The combined extracts were washed with brine, dried over Na2SO4. and evaporated in vacuo. The crude product was purified by flash chromatography (0-60% EtOc/hexanes) to afford the title compound as a white solid (1.4 g, 56%). 1HNMR (CDCl3): δ 8.04 (d, 1H), 7.83-7.81 (m, 1H), 7.74-7.71 (m, 1H), 7.57-7.52 (m, 3H), 7.48-7.44 (m, 2H), 7.20 (d, 1H), 6.74 (d, 1H), 6.63 (s, 1H), 3.07 (s, 3H), 2.42 (brs, 1H), 2.20-1.83 (m, 8H). MS(ES) 499 [M+H]+, 481 (M-OH).

Workup

  1. customdid not rise above 40° C
  2. additionwas added
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customand evaporated in vacuo
  7. customThe crude product was purified by flash chromatography (0-60% EtOc/hexanes)

Sources & evidence

ORD record
ord-98685b03ab214ee59373495063fce9b7
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