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

HRID 1173827노트

반응식

HRID 1173827 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 178455349HCID 178455349, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-337d866f82844ca1b7bbace6616bec74
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834194B2

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