Sodium Carbonate → HCID 57786721, compound

HRID 1969119Notes

Reaction equation

HRID 1969119 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[CH3:12][C:13]1[C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][CH:16]=[CH:15][C:14]=1[NH:28][C:29]([N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)=[O:30].C(=O)([O-])[O-].[Na+].[Na+].CO.C(Cl)Cl>COCCOC.O.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>[NH2:11][C:4]1[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=[C:2]([C:18]2[C:13]([CH3:12])=[C:14]([NH:28][C:29]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])[CH:15]=[CH:16][CH:17]=2)[CH:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 177503946-Bromoimidazo[1,2-a]pyridin-8-amineHCID 21226129Dichloromethane methanolHCID 57786672HCID 57786672, compound

Product 1

HCID 57786721HCID 57786721, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

The mixture of 105 mg (0.493 mmol) of 6-Bromo-imidazo[1,2-a]pyridin-8-ylamine, 195 mg (0.591 mmol) of Pyrrolidine-1-carboxylic acid [2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amide, 157 mg (1.48 mmol) of sodium carbonate, and 57 mg (0.049 mmol) of tetrakis(triphenylphosphine)palladium in 5 mL of 1,2-dimethoxyethane and 2.5 mL of water was heated at 110 C for 30 minutes using microwave. The mixture was partitioned between 50 mL of ethyl acetate and 10 mL of water. The organic layer was dried (MgSO4), and concentrated. Column chromatography (0->10% MeOH/CH2Cl2 in 20 minutes) gave 104 mg (0.310 mmol, 63%) of the title compound.

Workup

  1. temperaturewas heated at 110 C for 30 minutes
  2. customThe mixture was partitioned between 50 mL of ethyl acetate and 10 mL of water
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7cc35c8c935f4eba8d9316f349b223b4
Source dataset
uspto-grants-2013_04
Patent number
US08426441B2

Reaction notes

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