Potassium Carbonate → HCID 178502478, compound

HRID 1751345Notes

Reaction equation

HRID 1751345 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:30](=[CH:31][CH:32]=1)[C:8]1[NH:9][C:10]([C@@H:12]3[C@@H:17]4[CH2:18][C@@H:14]([CH2:15][CH2:16]4)[N:13]3[C:19](=[O:29])[C@@H:20]([NH:24][C:25](=[O:28])[O:26][CH3:27])[CH:21]([CH3:23])[CH3:22])=[N:11][C:7]=1[CH:6]=[CH:5]2.CC1(C)C(C)(C)OB([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[NH:51][C:50]([C@@H:52]4[CH2:56][CH2:55][CH2:54][N:53]4[C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])=[N:49][CH:48]=3)=[CH:43][CH:42]=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>[CH3:27][O:26][C:25]([NH:24][C@@H:20]([CH:21]([CH3:23])[CH3:22])[C:19]([N:13]1[C@H:12]([C:10]2[NH:9][C:8]3[C:30]4[C:4]([CH:5]=[CH:6][C:7]=3[N:11]=2)=[CH:3][C:2]([C:41]2[CH:42]=[CH:43][C:44]([C:47]3[NH:51][C:50]([C@@H:52]5[CH2:56][CH2:55][CH2:54][N:53]5[C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])=[N:49][CH:48]=3)=[CH:45][CH:46]=2)=[CH:32][CH:31]=4)[C@@H:17]2[CH2:18][C@H:14]1[CH2:15][CH2:16]2)=[O:29])=[O:28]

Participants

6

Reactant 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 178502472HCID 178502472, compound

Product 1

HCID 178502478HCID 178502478, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

Methyl (S)-1-((1R,3S,4S)-3-(7-bromo-1H-naphtho[1,2-d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-3-methyl-1-oxobutan-2-ylcarbamate (122 mg, 0.24 mmol) and (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 (114 mg, 0.26 mmol) were combined in DME (3 mL). Pd(PPh3)4 (28 mg, 0.024 mmol) and K2CO3 (2M H2O, 0.4 mL, 0.79 mmol) were added, and the solution was degassed with N2 for 10 min. The solution was heated to 85° C. and stirred o/n. The following morning, the solution was cooled to rt. The solution was diluted with EtOAc, washed with sat. NaHCO3, brine, dried with MgSO4, and concentrated. The residue was purified by silica gel chromatography to yield product (73 mg).

Workup

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

Sources & evidence

ORD record
ord-02a56fe7e30b4a1995c1efa7b94da2a2
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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