Potassium Carbonate → HCID 178502416, 화합물

HRID 1751419노트

반응식

HRID 1751419 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:31](=[CH:32][CH:33]=2)[C:15]2[NH:16][C:17]([C@@H:19]4[CH2:23][CH2:22][CH2:21][N:20]4[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:18][C:14]=2[CH2:13][CH2:12]3)O1.Br[C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][CH:45]=1)[CH:42]=[C:41]([C:46]1[NH:50][C:49]([C@@H:51]3[CH2:55][CH2:54][CH2:53][N:52]3[C:56](=[O:66])[C@@H:57]([NH:61][C:62](=[O:65])[O:63][CH3:64])[CH:58]([CH3:60])[CH3:59])=[N:48][CH:47]=1)[CH:40]=[CH:39]2.C([O-])([O-])=O.[K+].[K+]>COCCOC.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>[CH3:64][O:63][C:62]([NH:61][C@@H:57]([CH:58]([CH3:60])[CH3:59])[C:56]([N:52]1[CH2:53][CH2:54][CH2:55][C@H:51]1[C:49]1[NH:50][C:46]([C:41]2[CH:42]=[C:43]3[C:38](=[CH:39][CH:40]=2)[CH:37]=[C:36]([C:9]2[CH:10]=[C:11]4[C:31](=[CH:32][CH:33]=2)[C:15]2[NH:16][C:17]([C@@H:19]5[CH2:23][CH2:22][CH2:21][N:20]5[C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])=[N:18][C:14]=2[CH2:13][CH2:12]4)[CH:45]=[CH:44]3)=[CH:47][N:48]=1)=[O:66])=[O:65]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 59610262methyl (S)-1-((S)-2-(5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamateHCID 178451905HCID 178451905, 화합물

생성물 1

HCID 178502416HCID 178502416, 화합물수율 55.4%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
85 °C

실험 절차

(S)-tert-butyl 2-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dihydro-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (574 mg, 1.23 mmol), methyl (S)-1-((S)-2-(5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (616 mg, 1.23 mmol), Pd(PPh3)4 (142 mg, 0.123 mmol), and K2CO3 (2M in H2O, 1.2 mL, 2.4 mmol) were combined in DME. The reaction mixture was degassed with bubbling N2 for 10 min, then heated to 85° C. After 16 h, the reaction mixture was cooled to RT and concentrated. The crude residue was purified by silica column chromatography (0% to 30% MeOH/EtOAc) to afford the title compound (516 mg, 55%).

후처리

  1. customThe reaction mixture was degassed with bubbling N2 for 10 min
  2. temperaturethe reaction mixture was cooled to RT
  3. concentrationconcentrated
  4. customThe crude residue was purified by silica column chromatography (0% to 30% MeOH/EtOAc)

출처 및 근거

ORD 기록
ord-89f5db7c270d4c628519de2808fa79a9
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156823B2

반응 노트

불러오는 중…