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Sodium Carbonate → HCID 178432609、化合物

HRID 1530630
ノート
印刷プレビュー

反応式

HRID 1530630 の反応式
Br[C:2]1[CH:3]=[N:4][N:5]([CH3:19])[C:6]=1[CH:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]1.[CH3:20][C:21]1[N:25]=[C:24]([C:26]2[N:27]=[C:28]3[N:38]([CH:39]=2)[CH2:37][CH2:36][O:35][C:34]2[C:29]3=[CH:30][CH:31]=[C:32](B3OC(C)(C)C(C)(C)O3)[CH:33]=2)[N:23]([CH:49]([CH3:51])[CH3:50])[N:22]=1.C([O-])([O-])=O.[Na+].[Na+]>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:15]([O:14]1[CH2:8][CH:7]([C:6]2[N:5]([CH3:19])[N:4]=[CH:3][C:2]=2[C:32]2[CH:33]=[C:34]3[C:29](=[CH:30][CH:31]=2)[C:28]2[N:38]([CH:39]=[C:26]([C:24]4[N:23]([CH:49]([CH3:50])[CH3:51])[N:22]=[C:21]([CH3:20])[N:25]=4)[N:27]=2)[CH2:37][CH2:36][O:35]3)[CH2:11][CH2:10][NH:9][C:12]1=[O:13])([CH3:18])([CH3:17])[CH3:16]
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 10340Sodium CarbonateHCID 582043852-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-8-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azuleneHCID 68313064tert-butyl 3-(4-bromo-1-methyl-1H-pyrazol-5-yl)pyrrolidine-1-carboxylate

生成物 1

HCID 178432609HCID 178432609、化合物収率 46%

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

A mixture of tert-butyl 3-(4-bromo-1-methyl-1H-pyrazol-5-yl)pyrrolidine-1-carboxylate (1.0 g, 3.1 mmol), 4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-12-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1 (14),2,4,10,12-pentaene (1.1 g, 2.5 mmol), Pd(dppf)Cl2 (310 mg, 0.379 mmol), and Na2CO3 (1.34 g, 12.6 mmol) in dioxane (20 mL) was stirred at 80° C. for 16 h. The resultant mixture was extracted with ethyl acetate (50 mL), washed with brine, dried over MgSO4, filtered, and evaporated to afford the crude product, which was purified by reverse phase Combiflash eluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3 to give 1-tert-butyl-6-(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-oxazepan-2-one (920 mg, 46% yield) as white solid. LCMS (ESI) m/z: 559.4 [M+H+]. 1H-NMR (500 MHz, DMSO-d6) δ 8.41 (d, J=8.5 Hz, 1H), 7.91 (s, 1H), 7.48 (s, 1H), 7.09 (d, J=8.5 Hz, 1H), 6.96 (s, 1H), 5.88-5.85 (m, 1H), 4.53 (s, 4H), 3.75 (s, 3H), 3.72 (s, 1H), 3.60 (s, 1H), 3.51-3.42 (m, 2H), 3.24-3.20 (m, 1H), 2.26 (s, 3H), 2.15-2.07 (m, 2H), 1.46 (s, 6H), 1.37 (s, 9H).

後処理

  1. extractionThe resultant mixture was extracted with ethyl acetate (50 mL)
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford the crude product, which
  7. customwas purified by reverse phase Combiflash
  8. washeluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3

出典と根拠

ORDレコード
ord-13f5d3b2f1aa4f6eaa742a7e52356ebb
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