Potassium Carbonate → HCID 86705197, compound

HRID 2401290Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[CH2:10][N:11]2[C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:14][N:13]([C:20]3[CH:21]=[N:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=3)[C:12]2=[O:30])=[CH:4][CH:3]=1.[CH:32]1(B(O)O)[CH2:34][CH2:33]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:32]1([C:2]2[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[CH2:10][N:11]3[C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:14][N:13]([C:20]4[CH:21]=[N:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=4)[C:12]3=[O:30])=[CH:4][CH:3]=2)[CH2:34][CH2:33]1

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of N-(6-bromopyridin-3-yl)-2-{(5S)-5-(2-methylpropyl)-2-oxo-3-[6-(trifluoromethyl)pyridin-3-yl]imidazolidin-1-yl}acetamide (50 mg), cyclopropyl boronic acid (17 mg), palladium acetate (1.1 mg), triphenylphosphine (2.6 mg), and potassium carbonate (41 mg) in toluene/water (=20:1, 1.5 mL) was stirred at 110° C. for 9 hr. Additional cyclopropyl boronic acid (35 mg) was added thereto, and the mixture was further stirred at 110° C. for 6 hr, followed by at 80° C. for 2 hr. The solvent was distilled off under reduced pressure, and the residue was purified by preparative HPLC. After further purification by PTLC(NH silica gel, hexane/ethyl acetate=1:1), the resulting solid was washed with isopropyl ether to afford the title compound (2.5 mg).

Workup

waitfollowed by at 80° C. for 2 hr
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by preparative HPLC
customAfter further purification by PTLC(NH silica gel, hexane/ethyl acetate=1:1), the resulting solid
washwas washed with isopropyl ether

Sources & evidence

ORD record: ord-3603084d7bcd4979bc0568fece1ec408
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796272B2

Reaction notes

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