2-(Bromomethyl)-3-chloro-1-benzothiophene → HCID 178455349, compound

HRID 1173827Notes

Reaction equation

HRID 1173827 reaction equation
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=[O:19])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[Li+].CC([N-]C(C)C)C.Br[CH2:31][C:32]1[S:36][C:35]2[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=2[C:33]=1[Cl:41]>C1COCC1>[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([CH2:31][C:32]3[S:36][C:35]4[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=4[C:33]=3[Cl:41])[C:14]2=[O:19])[CH2:11][CH2:12]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8167082-(Bromomethyl)-3-chloro-1-benzothiopheneHCID 2724682Lithium diisopropylamideHCID 178455338HCID 178455338, compound

Product 1

HCID 178455349HCID 178455349, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Place trans-1-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-piperidin-2-one, (300 mg, 0.96 mmol) in 7.0 mL of THF, cool to −78° C. and treat with 2.0 M LDA (0.72 mL, 1.5 mmol). Stir for 5.0 minutes, treat with 2-bromomethyl-3-chloro-benzo[b]thiophene (375 mg, 1.5 mmol) and stir overnight at room temperature. Quench reaction with ammonium chloride, extract with dichloromethane, dry over sodium sulfate and purify via silica chromatography (ethyl acetate/hexanes 0-25%) affords 310 mg (65

Workup

  1. stirringstir overnight at room temperature
  2. customQuench
  3. customreaction with ammonium chloride
  4. extractionextract with dichloromethane
  5. dry with materialdry over sodium sulfate
  6. custompurify via silica chromatography (ethyl acetate/hexanes 0-25%)
  7. customaffords 310 mg (65

Sources & evidence

ORD record
ord-337d866f82844ca1b7bbace6616bec74
Source dataset
uspto-grants-2010_11
Patent number
US07834194B2

Reaction notes

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