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Potassium Carbonate → HCID 178432608、化合物

HRID 1530605
ノート
印刷プレビュー

反応式

HRID 1530605 の反応式
Br[C:2]1[CH:3]=[N:4][N:5]([CH3:20])[C:6]=1[CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1.[CH3:21][C:22]1[N:26]=[C:25]([C:27]2[N:28]=[C:29]3[N:39]([CH:40]=2)[CH2:38][CH2:37][O:36][C:35]2[C:30]3=[CH:31][CH:32]=[C:33](B(O)O)[CH:34]=2)[N:24]([CH:44]([CH3:46])[CH3:45])[N:23]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:16]([O:15]1[CH2:10][CH2:11][CH2:12][CH:7]([C:6]2[N:5]([CH3:20])[N:4]=[CH:3][C:2]=2[C:33]2[CH:34]=[C:35]3[C:30](=[CH:31][CH:32]=2)[C:29]2[N:39]([CH:40]=[C:27]([C:25]4[N:24]([CH:44]([CH3:45])[CH3:46])[N:23]=[C:22]([CH3:21])[N:26]=4)[N:28]=2)[CH2:38][CH2:37][O:36]3)[CH2:8][NH:9][C:13]1=[O:14])([CH3:19])([CH3:18])[CH3:17]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 68313095{4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}boronic acidHCID 68313245tert-Butyl 3-(4-bromo-1-methyl-1H-pyrazol-5-yl)piperidine-1-carboxylate

生成物 1

HCID 178432608HCID 178432608、化合物収率 50%

試薬・触媒・溶媒 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To a solution of tert-butyl 3-(4-bromo-1-methyl-1H-pyrazol-5-yl)piperidine-1-carboxylate (680 mg, 1.98 mmol) in dioxane (20.0 mL), was added {4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}boronic acid (660 mg, 1.87 mmol), K2CO3 (780 mg, 5.70 mmol), and Pd(dppf)Cl2 (117 mg, 0.19 mmol). The resulting mixture was stirred at 80° C. for 18 h. After concentration, the residue was diluted with EtOAc (20 mL) and washed with brine (20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel chromatography eluting with a 0-20% gradient of EtOAc in petroleum ether to give 1-tert-butyl-5-(1-methyl-4-{4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}-1H-pyrazol-5-yl)-λ3,3-oxazocan-2-one (540 mg, 50% yield) as a yellow solid. LCMS (ESI) m/z: 573.4 [M+H+].

後処理

  1. concentrationAfter concentration
  2. additionthe residue was diluted with EtOAc (20 mL)
  3. washwashed with brine (20 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a 0-20% gradient of EtOAc in petroleum ether

出典と根拠

ORDレコード
ord-ef324a77f44e4cc7ba8b2b9c9d19269e
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090628B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート