Potassium Carbonate → HCID 178502349、化合物

HRID 1751424ノート

反応式

HRID 1751424 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:31](=[CH:32][CH:33]=1)[C:8]1[NH:9][C:10]([C@@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:17](=[O:30])[C@@H:18]([NH:25][C:26](=[O:29])[O:27][CH3:28])[CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:11][C:7]=1[CH2:6][CH2:5]2.CC1(C)C(C)(C)OB([C:42]2[CH:43]=[C:44]3[C:49](=[CH:50][CH:51]=2)[CH:48]=[C:47]([C:52]2[NH:56][C:55]([C@@H:57]4[CH2:61][CH2:60][CH2:59][N:58]4[C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])=[N:54][CH:53]=2)[CH:46]=[CH:45]3)O1.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>[CH3:28][O:27][C:26]([NH:25][C@@H:18]([CH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[C:17]([N:13]1[CH2:14][CH2:15][CH2:16][C@H:12]1[C:10]1[NH:9][C:8]2[C:31]3[C:4]([CH2:5][CH2:6][C:7]=2[N:11]=1)=[CH:3][C:2]([C:42]1[CH:43]=[C:44]2[C:49](=[CH:50][CH:51]=1)[CH:48]=[C:47]([C:52]1[NH:56][C:55]([C@@H:57]4[CH2:61][CH2:60][CH2:59][N:58]4[C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])=[N:54][CH:53]=1)[CH:46]=[CH:45]2)=[CH:33][CH:32]=3)=[O:30])=[O:29]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 584986761,1-Dimethylethyl (2S)-2-[5-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthalenyl]-1H-imidazol-2-yl]-1-pyrrolidinecarboxylateHCID 178502347HCID 178502347、化合物

生成物 1

HCID 178502349HCID 178502349、化合物収率 40%

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

Methyl (S)-2-((S)-2-(7-bromo-4,5-dihydro-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidin-1-yl)-2-oxo-1-(tetrahydro-2H-pyran-4-yl)ethylcarbamate (211 mg, 0.408 mmol), (S)-tert-butyl 2-(5-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (220 mg, 0.449 mmol), Pd(PPh3)4 (47 mg, 0.0408 mmol) and K2CO3 (2M in H2O, 0.45 mL, 0.9 mmol) were suspended in DME (4 mL). The reaction mixture was degassed for 10 min with N2 then heated to 85° C. After 17 h, it was cooled to RT, diluted with MeOH, filtered over a thiol SPE column and concentrated. The crude residue was purified by silica column chromatography (0% to 40% MeOH/EtOAc) to afford the title compound (130 mg, 40%).

後処理

  1. customThe reaction mixture was degassed for 10 min with N2
  2. temperatureit was cooled to RT
  3. additiondiluted with MeOH
  4. filtrationfiltered over a thiol SPE column
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica column chromatography (0% to 40% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-0298525bd7f64d26855f9324bbdd4756
出典データセット
uspto-grants-2015_10
特許番号
US09156823B2

反応ノート

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