2-(Bromomethyl)-3-chloro-1-benzothiophene → HCID 178455348, 화합물

HRID 1173828노트

반응식

HRID 1173828 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 178455337HCID 178455337, 화합물

생성물 1

HCID 178455348HCID 178455348, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Place cis-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 (250 mg, 0.96 mmol) and stir at −78° C. for five hours, and warm to 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 166 mg (35%).

후처리

  1. stirringstir at −78° C. for five hours
  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 166 mg (35%)

출처 및 근거

ORD 기록
ord-8079d06e04884046b95614864e6d74fd
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834194B2

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