Potassium Carbonate → HCID 69675721, compound

HRID 1751410Notes

Reaction equation

HRID 1751410 reaction equation
[CH3:1][O:2][C:3](=[O:43])[NH:4][CH:5]([CH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)[C:6](=[O:36])[N:7]1[CH2:11][CH2:10][CH2:9][CH:8]1[C:12]1[NH:13][C:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22](B4OC(C)(C)C(C)(C)O4)[CH:23]=3)[CH:18]=2)=[CH:15][N:16]=1.[C:44]([O:48][C:49](=[O:61])[NH:50][CH2:51][C:52]([C:54]1[CH:59]=[CH:58][C:57](Br)=[CH:56][CH:55]=1)=[O:53])([CH3:47])([CH3:46])[CH3:45].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:43])[NH:4][CH:5]([CH:37]1[CH2:38][CH2:39][O:40][CH2:41][CH2:42]1)[C:6]([N:7]1[CH2:11][CH2:10][CH2:9][CH:8]1[C:12]1[NH:13][C:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:57]4[CH:58]=[CH:59][C:54]([C:52](=[O:53])[CH2:51][NH:50][C:49]([O:48][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:61])=[CH:55][CH:56]=4)[CH:23]=3)[CH:18]=2)=[CH:15][N:16]=1)=[O:36]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 59610197tert-Butyl [2-(4-bromophenyl)-2-oxoethyl]carbamateHCID 69675202[2-Oxo-1-(tetrahydro-pyran-4-yl)-2-(2-{5-[6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidin-1-yl)-ethyl]-carbamic acid methyl ester

Product 1

HCID 69675721HCID 69675721, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

[2-Oxo-1-(tetrahydro-pyran-4-yl)-2-(2-{5-[6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidin-1-yl)-ethyl]-carbamic acid methyl ester (200 mg, 0.34 mmol), [2-(4-Bromo-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (106 mg, 0.34 mmol), Pd[PPh3]4 (39.2 mg, 0.034 mmol), potassium carbonate (117 mg, 0.85 mmol) was heated at 120 C in the microwave for 22 minutes in DME (2.5 mL) and water (0.3 mL). Brine (1 mL) was added and the organic layer was isolated and the volatiles were removed. The product was purified via flash chromatography on silica gel (eluent: EtOAc/hexanes) to yield 183 mg.

Workup

  1. customthe organic layer was isolated
  2. customthe volatiles were removed
  3. customThe product was purified via flash chromatography on silica gel (eluent: EtOAc/hexanes)
  4. customto yield 183 mg

Sources & evidence

ORD record
ord-ad3a86b403ba406aa39a4c09ab303399
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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