6-Bromoimidazo[1,2-a]pyridin-8-amine → HCID 42643655, compound

HRID 1969109Notes

Reaction equation

HRID 1969109 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.[C:12]([C:16]1[CH:40]=[CH:39][C:19]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25](B3OC(C)(C)C(C)(C)O3)[C:24]=2[CH3:38])=[O:21])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]>C([O-])([O-])=O.[Na+].[Na+].COCCOC.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:25]2[C:24]([CH3:38])=[C:23]([NH:22][C:20](=[O:21])[C:19]3[CH:18]=[CH:17][C:16]([C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:40][CH:39]=3)[CH:28]=[CH:27][CH:26]=2)[CH:3]=1

Participants

6

Reactant 2

HCID 177503946-Bromoimidazo[1,2-a]pyridin-8-amineHCID 587289934-(tert-Butyl)-N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide

Product 1

HCID 42643655HCID 42643655, compoundYield 67.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 6-Bromo-imidazo[1,2-a]pyridin-8-ylamine (0.72 g, 3.43 mmol), 4-tert-Butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane-2-yl)-phenyl]-benzamide (1.0 g, 2.54 mmol), Pd(PPh3)4 (0.29 g, 0.25 mmol) in 5 ml 1M Na2CO3 and 10 mL of ethylene glycol dimethyl ether was stirred at 170° C. in a microwave for 20 min. The resulting suspension was filtered through celite and then partitioned between 100 mL of water and 100 mL of ethyl acetate, and the aqueous layer was further extracted with 50 mL of ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated to a residue. Column chromatography (0-6% MeOH/CH2Cl2) afforded 0.685 g of product.

Workup

  1. filtrationThe resulting suspension was filtered through celite
  2. custompartitioned between 100 mL of water and 100 mL of ethyl acetate
  3. extractionthe aqueous layer was further extracted with 50 mL of ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-0ca32b444b21462cb6e9beb3d4753ea4
Source dataset
uspto-grants-2013_04
Patent number
US08426441B2

Reaction notes

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