Potassium Phosphate, Tribasic → Tert-butyl {1-[4-(5-methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutyl}carbamate

HRID 872365Notes

Reaction equation

HRID 872365 reaction equation
Br[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[N:5]2[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC1(C)C(C)(C)OB([C:26]2[CH:31]=[CH:30][C:29]([C:32]3([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:35][CH2:34][CH2:33]3)=[CH:28][CH:27]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O>[CH3:10][C:6]1[N:5]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:2]([C:26]3[CH:27]=[CH:28][C:29]([C:32]4([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:41])([CH3:40])[CH3:42])[CH2:33][CH2:34][CH2:35]4)=[CH:30][CH:31]=3)[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 58326444tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamateHCID 666657172-Bromo-5-methyl-3-phenylimidazo[1,2-A]pyridine

Product 1

HCID 86691044Tert-butyl {1-[4-(5-methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutyl}carbamateYield 83.1%

Reagents, catalysts & solvents 1

HCID 86587398Ethanol toluene waterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-bromo-5-methyl-3-phenylimidazo[1,2-a]pyridine (38 mg, 0.13 mmol), tert-butyl {1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclobutyl}carbamate (see step 4, 64 mg, 0.17 mmol) and potassium phosphate (84.3 mg, 0.40 mmol) in 1.2 ml toluene/ethanol/water (1/2/1) was heated to 120° C. in a single mode microwave reactor (Biotage). This experiment was repeated employing the same protocol. Both reaction mixtures were combined and partitioned between dichloromethane and water. The mixture was filtered through a phase separator and concentrated in vacuo. The crude material was purified by column chromatography (Snap cartridge, hexane/ethyl acetate 95/5->hexane/ethyl acetate 1/1) to give 49 mg of the title compound (34% overall yield).

Workup

  1. customBoth reaction mixtures
  2. custompartitioned between dichloromethane and water
  3. filtrationThe mixture was filtered through a phase separator
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by column chromatography (Snap cartridge, hexane/ethyl acetate 95/5->hexane/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-e11d009a60864f72ad4106c0c74dd47e
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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