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Potassium Carbonate → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(6-(1-methyl-1H-indazol-5-yl)pyridin-2-yl)benzo[d]thiazol-6-yl)acetate

HRID 879550
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인쇄 미리보기

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HRID 879550 반응식
[C:1]([O:5][C@@H:6]([C:12]1[C:36]([CH3:37])=[CH:35][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4[CH:26]=[C:27]5[C:31](=[CH:32][CH:33]=4)[N:30]([CH3:34])[N:29]=[CH:28]5)[N:20]=3)[S:18][C:14]=2[C:13]=1OS(C(F)(F)F)(=O)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[Cl:46][C:47]1[CH:52]=[CH:51][C:50](B(O)O)=[CH:49][CH:48]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.CCOC(C)=O.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>[C:1]([O:5][C@@H:6]([C:12]1[C:36]([CH3:37])=[CH:35][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]4[CH:26]=[C:27]5[C:31](=[CH:32][CH:33]=4)[N:30]([CH3:34])[N:29]=[CH:28]5)[N:20]=3)[S:18][C:14]=2[C:13]=1[C:50]1[CH:51]=[CH:52][C:47]([Cl:46])=[CH:48][CH:49]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 86700372(S)-ethyl 2-tert-butoxy-2-(5-methyl-2-(6-(1-methyl-1H-indazol-5-yl)pyridin-2-yl)-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)acetate

생성물 1

HCID 86700374(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(6-(1-methyl-1H-indazol-5-yl)pyridin-2-yl)benzo[d]thiazol-6-yl)acetate

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

In a 10 mL reaction vial, (S)-ethyl 2-tert-butoxy-2-(5-methyl-2-(6-(1-methyl-1H-indazol-5-yl)pyridin-2-yl)-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)acetate (33 mg, 0.050 mmol) and p-chlorophenyl boronic acid (48 mg, 0.20 mmol) were dissolved in dioxane (2.5 mL) under argon atmosphere. The solution was bubbled with argon for 5 min. Then potassium carbonate (45 mg, 0.32 mmol) and Pd(PPh3)4 (10 mg, 0.0075 mmol) were added sequentially. The reaction mixture was sealed and heated in oil bath at 120° C. for 4.5 h. Reaction was then diluted with EtOAc (10 mL) and filtered to remove solid. The filtrate was concentrated and purified on silica gel column with 0-40% EtOAc/Hex to afford product. LCMS-ESI+: calc'd for: C35H33ClN4O3S: 625.2, 626.2, 627.2 (M+H+); found: 625.1, 626.2, 627.1 (M+H+).

후처리

  1. customIn a 10 mL reaction vial
  2. customThe solution was bubbled with argon for 5 min
  3. customThe reaction mixture was sealed
  4. customReaction
  5. filtrationfiltered
  6. customto remove solid
  7. concentrationThe filtrate was concentrated
  8. custompurified on silica gel column with 0-40% EtOAc/Hex
  9. customto afford product

출처 및 근거

ORD 기록
ord-894df2a2a25e422c8f20dd0b51dae54b
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987250B2

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