Potassium Carbonate → HCID 86708705、化合物

HRID 1751330ノート

反応式

HRID 1751330 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[NH:16][C:15]([C@@H:17]3[CH2:21][C@H:20]([OH:22])[CH2:19][N:18]3[C:23](=[O:33])[C@@H:24]([NH:28][C:29](=[O:32])[O:30][CH3:31])[CH:25]([CH3:27])[CH3:26])=[N:14][CH:13]=1)[CH:6]=[CH:5]2.CC1(C)C(C)(C)OB([C:42]2[CH:47]=[CH:46][C:45]([C:48]3[NH:52][C:51]([C@@H:53]4[CH2:57][CH2:56][CH2:55][N:54]4[C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])=[N:50][CH:49]=3)=[CH:44][CH:43]=2)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>[OH:22][C@@H:20]1[CH2:19][N:18]([C:23](=[O:33])[C@@H:24]([NH:28][C:29]([O:30][CH3:31])=[O:32])[CH:25]([CH3:26])[CH3:27])[C@H:17]([C:15]2[NH:16][C:12]([C:7]3[CH:8]=[C:9]4[C:4](=[CH:5][CH:6]=3)[CH:3]=[C:2]([C:42]3[CH:43]=[CH:44][C:45]([C:48]5[NH:52][C:51]([C@@H:53]6[CH2:57][CH2:56][CH2:55][N:54]6[C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])=[N:50][CH:49]=5)=[CH:46][CH:47]=3)[CH:11]=[CH:10]4)=[CH:13][N:14]=2)[CH2:21]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 56605289(s)-tert-Butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1h-imidazol-2-yl)pyrrolidine-1-carboxylateHCID 86708706methyl (S)-1-((2S,4S)-2-(5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl)-4-hydroxypyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

生成物 1

HCID 86708705HCID 86708705、化合物収率 42.9%

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

To a solution of methyl (S)-1-((2S,4S)-2-(5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl)-4-hydroxypyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (100 mg, 0.19 mmol) in DME (2 mL) was added (S)-tert-butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (83 mg, 0.19 mmol), Pd(PPh3)4 (22 mg, 0.019 mmol), and K2CO3 (2M in H2O, 0.32 mL, 0.63 mmol). The solution was degassed with N2 for 10 min, then heated to 85° C. for 18 h. The mixture was cooled to rt, diluted with EtOAc, and washed with sat. NaHCO3, brine, dried over MgSO4, and concentrated. The residue was purified by silica gel chromatography to yield product (61 mg).

後処理

  1. customThe solution was degassed with N2 for 10 min
  2. temperatureThe mixture was cooled to rt
  3. additiondiluted with EtOAc
  4. washwashed with sat. NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-9ade54a0e29d42dfb0845437dddd24f3
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…