Potassium Carbonate → HCID 86708705, 화합물

HRID 1751330노트

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HRID 1751330 반응식
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

참가 물질

6

반응물 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

생성물 1

HCID 86708705HCID 86708705, 화합물수율 42.9%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

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온도
85 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9ade54a0e29d42dfb0845437dddd24f3
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156823B2

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