Potassium Carbonate → HCID 67960123、化合物

HRID 1529407ノート

反応式

HRID 1529407 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 67960123HCID 67960123、化合物収率 59.7%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  1. customThe crude was purified

出典と根拠

ORDレコード
ord-3c30f1e6893941d18a53e36e9780d165
出典データセット
uspto-grants-2015_07
特許番号
US09090593B2

反応ノート

読み込み中…