Potassium Carbonate → HCID 178502423, compound

HRID 1751340Notes

Reaction equation

HRID 1751340 reaction equation
[CH3:1][CH:2]([CH3:36])[C@H:3]([NH:31][C:32](=[O:35])[O:33][CH3:34])[C:4](=[O:30])[N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[NH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18](B3OC(C)(C)C(C)(C)O3)=[CH:17][CH:16]=2)=[CH:13][N:14]=1.[C:37]([O:41][C:42]([N:44]1[C@H:49]([C:50]2[NH:54][C:53]3[C:55]4[C:60]([CH:61]=[CH:62][C:52]=3[N:51]=2)=[CH:59][C:58](Br)=[CH:57][CH:56]=4)[C@@H:48]2[CH2:64][C@H:45]1[CH2:46][CH2:47]2)=[O:43])([CH3:40])([CH3:39])[CH3:38].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>[C:37]([O:41][C:42]([N:44]1[C@H:49]([C:50]2[NH:54][C:53]3[C:55]4[C:60]([CH:61]=[CH:62][C:52]=3[N:51]=2)=[CH:59][C:58]([C:18]2[CH:19]=[CH:20][C:15]([C:12]3[NH:11][C:10]([C@@H:6]5[CH2:7][CH2:8][CH2:9][N:5]5[C:4](=[O:30])[C@@H:3]([NH:31][C:32]([O:33][CH3:34])=[O:35])[CH:2]([CH3:36])[CH3:1])=[N:14][CH:13]=3)=[CH:16][CH:17]=2)=[CH:57][CH:56]=4)[C@@H:48]2[CH2:64][C@H:45]1[CH2:46][CH2:47]2)=[O:43])([CH3:40])([CH3:39])[CH3:38]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 57462153Methyl ((S)-3-methyl-1-oxo-1-((S)-2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-yl)carbamateHCID 178452509HCID 178452509, compound

Product 1

HCID 178502423HCID 178502423, compoundYield 39.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

Methyl (S)-3-methyl-1-oxo-1-((S)-2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate (526 mg, 1.06 mmol) and (1R,3S,4S)-tert-butyl-3-(7-bromo-1H-naphtho[1,2-d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (427 mg, 0.96 mmol) were combined in DME (10 mL). Pd(PPh3)4 (111 mg, 0.096 mmol) and K2CO3 (2M H2O, 1.6 mL, 3.17 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 (280 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-3adb9c821a294798a66b217eb772836b
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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