Ammonium Chloride → {5-Cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfanyl)phenyl]methanol

HRID 70714노트

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HRID 70714 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C([Li])CCC.[CH:17]1([C:20]2[CH:21]=[CH:22][C:23]([CH:36]=[O:37])=[N:24][C:25]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH2:19][CH2:18]1.[Cl-].[NH4+]>O1CCCC1>[CH:17]1([C:20]2[CH:21]=[CH:22][C:23]([CH:36]([C:2]3[CH:7]=[CH:6][C:5]([S:8][CH:9]4[CH2:11][CH2:10]4)=[CH:4][CH:3]=3)[OH:37])=[N:24][C:25]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH2:18][CH2:19]1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 223501051-Bromo-4-cyclopropylthiobenzeneHCID 86658014HCID 86658014, 화합물HCID 178418339Butyllithium

생성물 1

HCID 67400247{5-Cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfanyl)phenyl]methanol수율 73.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of (4-bromophenyl)(cyclopropyl)sulfane (440 mg) in tetrahydrofuran (10 mL) was cooled to −78° C., and n-butyllithium (2.6 M, 0.74 mL) was slowly added dropwise, followed by stirring for 30 minutes. A solution of 5-cyclopropyl-6-[(4-methoxy benzyl)oxy]pyridine-2-carbaldehyde (417 mg) in tetrahydrofuran (5 mL) was slowly added dropwise, and the mixture was stirred at −78° C. for 4.5 hours. The reaction solution was stirred in an ice bath and a saturated ammonium chloride solution was added, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→62:38) to give {5-cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfanyl)phenyl]methanol as a yellow oil (469 mg, 73%).

후처리

  1. stirringthe mixture was stirred at −78° C. for 4.5 hours
  2. stirringThe reaction solution was stirred in an ice bath
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→62:38)

출처 및 근거

ORD 기록
ord-2ff5efe37b154b2497bcde72ffa813e7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

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