Potassium Carbonate → HCID 67960123, 화합물

HRID 1529407노트

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HRID 1529407 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[N:6]=[C:5]2[C:17]1[N:22]=[C:21]([O:23][C@H:24]2[CH2:31][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][CH2:28][C:25]32[CH2:27][CH2:26]3)[CH:20]=[N:19][CH:18]=1.[CH3:39][Si:40]([CH3:59])([CH3:58])[C:41]#[C:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[O:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]1[N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:48]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[C:42]#[C:41][Si:40]([CH3:39])([CH3:59])[CH3:58])=[CH:10][CH:9]=2)[C:5]([C:17]2[N:22]=[C:21]([O:23][C@H:24]3[CH2:31][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:36])[CH3:37])=[O:33])[CH2:29][CH2:28][C:25]43[CH2:26][CH2:27]4)[CH:20]=[N:19][CH:18]=2)=[N:6]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 46739757Trimethyl{[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethynyl}silaneHCID 67959732HCID 67959732, 화합물

생성물 1

HCID 67960123HCID 67960123, 화합물수율 59.7%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
160 °C

실험 절차

A mixture of (4R)-tert-butyl 4-(6-(5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate (159 mg, 0.272 mmol), trimethyl((2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethynyl)silane (123 mg, 0.408 mmol), PdCl2(Amphos) (19.26 mg, 0.027 mmol), and potassium carbonate (408 μL, 0.816 mmol) in dioxane (2720 μL) was heated in the microwave for 10 min at 160° C. The crude was purified via automated flash chromatography (silica gel) with 100% hexanes to 20% EtOAc/hexanes to give (4R)-tert-butyl 4-(6-(1-(tetrahydro-2H-pyran-2-yl)-5-(2-((trimethylsilyl)ethynyl)phenyl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate (110 mg, 0.162 mmol, 59.7% yield) as a yellowish oil. MS (ESI, pos. ion) m/z: 678.2 (M+1).

후처리

  1. customThe crude was purified

출처 및 근거

ORD 기록
ord-3c30f1e6893941d18a53e36e9780d165
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090593B2

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