Potassium Carbonate → HCID 59251367, compound

HRID 1466420Notes

Reaction equation

HRID 1466420 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[CH:10]=[C:11]([C:13]([OH:16])([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1.[CH3:25][S:26]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)(=[O:28])=[O:27].C([O-])([O-])=O.[K+].[K+]>COCCOC>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][N:9]1[CH:10]=[C:11]([C:13]([OH:16])([CH3:15])[CH3:14])[N:12]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([C:33]2[CH:32]=[CH:31][CH:30]=[C:29]([S:26]([CH3:25])(=[O:28])=[O:27])[CH:34]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 59251284HCID 59251284, compound

Product 1

HCID 59251367HCID 59251367, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-[2-(4-bromophenyl)-1-(2-chlorobenzyl)-1H-imidazol-4-yl]-propan-2-ol (130 mg, 0.32 mmol), 3-methanesulfonyl-phenylboronic acid (80 mg, 0.40 mmol), Cl2Pd(dppf)DCM (13 mg, 5 mol %) and a 2.8M aqueous solution of K2CO3 (0.35 mL, 0.98 mmol) in DME (2 mL) was heated in a microwave unit (Biotage Initiator™) at 120° C. for 4 min. The reaction mixture was concentrated and purified by chromatography (silica, EtOAc/Hex, 45:55 to 90:10) to give the title compound (118 mg, 77%) as a white solid. 1H-NMR. (DCM-d2): δ 8.08 (m, 1H), 7.84 (dd, 2H), 7.55-7.64 (m, 5H), 736 (m, 1H), 7.17-7.26 (m, 2H), 6.85 (d, 1H), 6.77 (s, 1H), 5.24 (s, 2H), 3.00 (s, 3H), 2.86 (br s, 1H), 1.49 (s, 6H); MS (ES): 481 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by chromatography (silica, EtOAc/Hex, 45:55 to 90:10)

Sources & evidence

ORD record
ord-fe6d6f4edec14ffcb57011289f8b3cb9
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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