1,2-Dibromo-1,1,2,2-tetrachloroethane → N-[3-(7-Benzenesulfonyl-6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide

HRID 589521Notes

Reaction equation

HRID 589521 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([C:19]4[C:20]([CH3:38])=[C:21]([NH:25][C:26](=[O:37])[C:27]5[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=5)[CH:22]=[CH:23][CH:24]=4)[C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].CC([N-]C(C)C)C.[Br:47]C(Cl)(Cl)C(Cl)(Cl)Br>C1COCC1>[C:1]1([S:7]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([C:19]4[C:20]([CH3:38])=[C:21]([NH:25][C:26](=[O:37])[C:27]5[CH:28]=[CH:29][C:30]([C:33]([CH3:34])([CH3:35])[CH3:36])=[CH:31][CH:32]=5)[CH:22]=[CH:23][CH:24]=4)[C:13]=3[CH:12]=[C:11]2[Br:47])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 694261,2-Dibromo-1,1,2,2-tetrachloroethaneHCID 2724682Lithium diisopropylamideHCID 71231472N-[3-(7-Benzenesulfonyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide

Product 1

HCID 71231447N-[3-(7-Benzenesulfonyl-6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of Intermediate 52 (4.26 g, 8.12 mmol) in THF (150 ml) at −78° C. was added LDA (1.5 M in THF, 16.24 ml, 24.36 mmol) slowly. The resulting mixture was stirred for 1.5 hrs at −78° C. before adding a solution of 1,2-dibromo-tetrachloroethane (3.97 g, 12.18 mmol) in THF (1 ml). Stirring was continued at −78° C. for 2 hrs, then the reaction mixture was quenched by addition of sat. aqueous NH4Cl solution and warmed up to r.t. The mixture was extracted with EtOAc and the organic layer was dried, filtered, and evaporated to dryness. Purification by flash chromatography (silica gel, cyclohexane/EtOAc gradient) yielded Intermediate 53.

Workup

  1. stirringStirring
  2. waitwas continued at −78° C. for 2 hrs
  3. customthe reaction mixture was quenched by addition of sat. aqueous NH4Cl solution
  4. temperaturewarmed up to r.t
  5. extractionThe mixture was extracted with EtOAc
  6. customthe organic layer was dried
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customPurification by flash chromatography (silica gel, cyclohexane/EtOAc gradient)

Sources & evidence

ORD record
ord-7bdbedabb69f4294ab2a732387823e1a
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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