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Lithium Hexamethyldisilazide → 3-(4-Bromo-2-chlorophenyl)-4-chloro-1-(cyclopropylsulfonyl)-1h-diimidazo[1,2-a:4',5'-d]pyridin-2(3h)-one

HRID 558214
Notes
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Reaction equation

HRID 558214 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][C:9]2=[O:21])=[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]([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[N:10]([S:36]([CH:33]3[CH2:35][CH2:34]3)(=[O:38])=[O:37])[C:9]2=[O:21])=[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 595194763-(4-Bromo-2-chlorophenyl)-4-chloro-1-(cyclopropylsulfonyl)-1h-diimidazo[1,2-a:4',5'-d]pyridin-2(3h)-one

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-ec248c5035df4dff89c929249870efe8
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063049B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes