Potassium Carbonate → HCID 178502416, compound

HRID 1751419Notes

Reaction equation

HRID 1751419 reaction equation
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]

Participants

6

Reactant 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, compound

Product 1

HCID 178502416HCID 178502416, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

(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%).

Workup

  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)

Sources & evidence

ORD record
ord-89f5db7c270d4c628519de2808fa79a9
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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