Potassium Carbonate → HCID 178502416、化合物

HRID 1751419ノート

反応式

HRID 1751419 の反応式
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]

参加物

6

反応物 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、化合物

生成物 1

HCID 178502416HCID 178502416、化合物収率 55.4%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

(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%).

後処理

  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)

出典と根拠

ORDレコード
ord-89f5db7c270d4c628519de2808fa79a9
出典データセット
uspto-grants-2015_10
特許番号
US09156823B2

反応ノート

読み込み中…