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Potassium Carbonate → (S)-3-{4-[2-(4-Cyano-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester

HRID 2272837
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HRID 2272837 반응식
Br[C:2]1[N:28]=[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][O:11][C:12]3[CH:17]=[CH:16][C:15]([C@@H:18]([C:25]#[C:26][CH3:27])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][CH:13]=3)=[CH:9][N:4]2[N:3]=1.CC1(C)C(C)(C)OB([C:37]2[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][CH:38]=2)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][C@@H:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:8]2[CH:7]=[CH:6][C:5]3[N:4]([N:3]=[C:2]([C:37]4[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][CH:38]=4)[N:28]=3)[CH:9]=2)=[CH:13][CH:14]=1)[C:25]#[C:26][CH3:27])[CH3:24]
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27346254-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileHCID 118151365Ethyl (3S)-3-[4-[(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methoxy]phenyl]hex-4-ynoate

생성물 1

HCID 118130002(S)-3-{4-[2-(4-Cyano-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester수율 73.2%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a stirred solution of ethyl (3S)-3-[4-[(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methoxy]phenyl]hex-4-ynoate (0.25 g, 0.57 mmol) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (0.14 g, 0.5 mmol) in dioxane (115 mL) is added K2CO3 (0.15 g, 1.134 mmol). The mixture is purged with argon for 30 minutes, Pd(PPh3)4 (0.032 g, 0.027 mmol) is added and the mixture is heated at 100° C. for 5 hours. The reaction mixture is cooled to room temperature, filtered through diatomaceous earth. The filtrate is evaporated under reduced pressure and concentrated to dryness. The crude material is purified by silica gel chromatography (combiflash) eluting with 30% EtOAc/hexane to give the title compound as a brown liquid (0.170 g, 68.75%). LCMS m/z 464 (M+H).

후처리

  1. customThe mixture is purged with argon for 30 minutes
  2. temperatureThe reaction mixture is cooled to room temperature
  3. filtrationfiltered through diatomaceous earth
  4. customThe filtrate is evaporated under reduced pressure
  5. concentrationconcentrated to dryness
  6. customThe crude material is purified by silica gel chromatography (combiflash)
  7. washeluting with 30% EtOAc/hexane

출처 및 근거

ORD 기록
ord-0418d728dc114017b4a0f4d0e2cec576
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09120793B2

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