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Lithium Hexamethyldisilazide → n-(7-(4-Bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridin-6-yl)cyclopropanesulfonamide

HRID 1161808
Notes
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Reaction equation

HRID 1161808 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[C:13]([Cl:20])[C:14]4[N:15]([CH:17]=[CH:18][N:19]=4)[CH:16]=[C:11]3[NH:10]C2=O)=[C:4]([Cl:22])[CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH:33]1([S:36](N)(=[O:38])=[O:37])[CH2:35][CH2:34]1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:12]2[C:11]([NH:10][S:36]([CH:33]3[CH2:35][CH2:34]3)(=[O:38])=[O:37])=[CH:16][N:15]3[CH:17]=[CH:18][N:19]=[C:14]3[C:13]=2[Cl:20])=[C:4]([Cl:22])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 15765418CyclopropanesulfonamideHCID 595194533-(4-Bromo-2-chlorophenyl)-4-chloro-1H-diimidazo[1,2-a:4',5'-d]pyridin-2(3H)-one

Product 1

HCID 57344032n-(7-(4-Bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridin-6-yl)cyclopropanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of the crude product (Step J) in 3 ml anhydrous THF was added LHMDS (0.4 ml, 0.4 mmol, 1M/THF) at 0° C. and the mixture was stirred for 5 min. The cyclopropyl sulfonamide (83 mg, 0.59 mol) was added neat and the mixture was warmed to room temperature and stirred for 15 h. The mixture was quenched with brine, diluted with H2O and extracted using a mixture of EtOAc/THF (3:1). The organic phase was washed with brine and dried with Na2SO4. Subsequent column chromatography (100% EtOAc) gave the title product as a brown oil (36 mg, 20% over the 2 last steps). Rf (100% EtOAc)=0.35. 1H-NMR (500 MHz, MeOH-D3): δ=8.80 (s, 1H), 7.89 (s, 1H), 7.86-7.85 (d, 1H), 7.68-7.66 (dd, 1H), 7.60-7.58 (d, 1H), 7.46 (s, 1H), 1.51-1.37 (m, 2H), 1.23-1.15 (m, 2H).

Workup

  1. stirringstirred for 15 h
  2. customThe mixture was quenched with brine
  3. additiondiluted with H2O
  4. extractionextracted
  5. additiona mixture of EtOAc/THF (3:1)
  6. washThe organic phase was washed with brine
  7. dry with materialdried with Na2SO4

Sources & evidence

ORD record
ord-5cf294abc3a04ab5b66888779d086790
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07820664B2

Reaction notes

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