Bromine → 5-Bromo-6-(3-methoxy-4-pyridin-2-ylphenyl)imidazo[2,1-b][1,3]thiazole

HRID 2213111Notes

Reaction equation

HRID 2213111 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:16]=[C:17]3[N:21]([CH:22]=2)[CH:20]=[CH:19][S:18]3)[CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[Br:23]Br>C(Cl)Cl>[Br:23][C:22]1[N:21]2[C:17]([S:18][CH:19]=[CH:20]2)=[N:16][C:15]=1[C:5]1[CH:6]=[CH:7][C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 9972490HCID 9972490, compound

Product 1

HCID 100915185-Bromo-6-(3-methoxy-4-pyridin-2-ylphenyl)imidazo[2,1-b][1,3]thiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 6-(3-methoxy-4-pyridin-2-ylphenyl)-imidazo[2,1-b][1,3]thiazole (100 mg, 0.33 mmol) in CH2Cl2 (3 mL) was treated with a solution of bromine (0.017 mL, 0.33 mmol) in CH2Cl2 (1 mL) over 1 h at 0° C. The reaction mixture was diluted with CH2Cl2 (25 mL) and was washed with a solution of saturated aqueous sodium bicarbonate (25 mL). The organic layer was dried (MgSO4) and concentrated to afford 5-bromo-6-(3-methoxy-4-pyridin-2-ylphenyl)imidazo[2,1-b][1,3]thiazole. 1H NMR (CD3OD, 500 MHz) δ 7.29 (d, 1H), 7.12 (dt, 1H), 6.82 (d, 1H), 6.47 (dd, 1H), 6.36 (s, 1H), 6.35 (dd, 1H), 6.27 (m, 2H), 5.83 (d, 1H), 2.49 (s, 3H) ppm. MS (ESI) 388 (M)+.

Workup

  1. washwas washed with a solution of saturated aqueous sodium bicarbonate (25 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3c02b500bfc942fba18c57f908e2a255
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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