Thiazole → HCID 5329345, compound

HRID 1245486Notes

Reaction equation

HRID 1245486 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:10][C:5]2=[N:4][CH:3]=1.[S:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.CC([O-])=O.[K+].CN(C)C(=O)C>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>[C:11]1([C:9]2[CH:8]=[CH:7][N:6]3[C:2]([C:21]4[S:17][CH:18]=[N:19][CH:20]=4)=[CH:3][N:4]=[C:5]3[CH:10]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 9256ThiazoleHCID 31374DimethylacetamideHCID 517044Potassium AcetateHCID 21912843HCID 21912843, compound

Product 1

HCID 5329345HCID 5329345, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A microwave vessel was charged with 3-bromo-7-phenylimidazo[1,2-a]pyridine (6-1, 0.050 g, 0.183 mmol), thiazole (0.065 ml, 0.92 mmol), tetrakis(triphenylphosphine)palladium(0) (0.011 g, 0.10 mmol) and KOAc (0.054 g, 0.55 mmol). N,N-dimethylacetamide, 1.5 ml, was added and the reaction was placed in the microwave reactor. The reaction was heated to 200° C. for 10 min. The reaction was diluted with water, and extracted 3× with DCM. The extracts were dried over Na2SO4, filtered and concentrated. The resulting residue was dissolved in DMSO and purified by reverse phase preparative HPLC. The resulting oil was triturated with ether, resulting in the rapid crystallization to a white solid. The solid was filtered and washed with ether. Afforded the pure title compound. 1H NMR (CDCl3) δ 9.11 (s, 1H), 8.47 (s, 1H), 8.37 (d, 1H, J=7.4 Hz), 8.20 (s, 1H), 8.00 (s, 1H), 7.73 (d, 2H, J=7.3 Hz), 7.57–7.52 (m, 4H). LCMS m/z (M+1) Calc: 278.1, found 278.1.

Workup

  1. extractionextracted 3× with DCM
  2. dry with materialThe extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe resulting residue was dissolved in DMSO
  6. custompurified by reverse phase preparative HPLC
  7. customThe resulting oil was triturated with ether
  8. customresulting in the rapid crystallization to a white solid
  9. filtrationThe solid was filtered
  10. washwashed with ether

Sources & evidence

ORD record
ord-67951b44ca374bcca758ce01adf01349
Source dataset
uspto-grants-2006_10
Patent number
US07125888B2

Reaction notes

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