Water → [4-(6-Bromo-imidazo[1,2-a]pyridin-8-ylamino)-phenyl]-morpholin-4-yl-methanone

HRID 402946Notes

Reaction equation

HRID 402946 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](I)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])=[CH:15][CH:14]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.O>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[O:20])=[CH:17][CH:18]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5778154-(Morpholine-4-carbonyl)anilineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 712991706-Bromo-8-iodoimidazo[1,2-a]pyridine

Product 1

HCID 86686844[4-(6-Bromo-imidazo[1,2-a]pyridin-8-ylamino)-phenyl]-morpholin-4-yl-methanoneYield 44%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

6-Bromo-8-iodo-imidazo[1,2-a]pyridine (500 mg, 1.53 mmol), (4-aminophenyl)(morpholino)-methanone (348 mg, 1.69 mmol) and CsCO3 (998 mg, 3.06 mmol) were dissolved in dioxane (10 ml). Under N2 atmosphere, Pd2(dba)3 (70 mg, 0.077 mmol) and Xantphos (89 mg, 0.153 mmol) were added and the mixture was stirred at reflux temperature overnight. After the completion of the reaction, the mixture was cooled to room temperature, poured into water (100 mL) and extracted with DCM (100 ml). The organic extracts were washed with saturated aqueous solution of sodium chloride (100 ml), dried over sodium sulfate and concentrated. The residue was purified by silica gel column (petroleum ether:ethyl acetate 1:2) to afford the desired product as a yellow solid (270 mg, yield 44%). LC-MS: 401[M+1]+, tR=1.257 min.

Workup

  1. temperatureat reflux temperature overnight
  2. customAfter the completion of the reaction
  3. extractionextracted with DCM (100 ml)
  4. washThe organic extracts were washed with saturated aqueous solution of sodium chloride (100 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column (petroleum ether:ethyl acetate 1:2)

Sources & evidence

ORD record
ord-5ff284bc9934410eb4da88ad7dba768a
Source dataset
uspto-grants-2014_06
Patent number
US08742098B2

Reaction notes

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