Potassium Carbonate → 2-(3,4-Dimethoxyphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazole

HRID 2409528Notes

Reaction equation

Br[C:2]1[S:6][C:5]2=[N:7][C:8]([CH3:10])=[CH:9][N:4]2[N:3]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20].C([O-])([O-])=O.[K+].[K+]>COCCOC.C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:2]2[S:6][C:5]3=[N:7][C:8]([CH3:10])=[CH:9][N:4]3[N:3]=2)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]

Participants

Conditions

Temperature: 130 °C

Procedure

To a mixture of 2-bromo-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole (0.550 g, 2.522 mmol, 1 eq), 3,4-dimethoxyphenylboronic acid (0.551 g, 3.026 mmol, 1.2 eq) and Pd(dppf)Cl2.DCM (0.209 g. 0.252 mmol, 0.1 eq) in DME (3 mL) was added K2CO3 (1 mL, sat. aq). The mixture was heated in the microwave oven (130° C., 1 h), cooled to RT, diluted with DCM, washed with water, dried (Na2SO4) and concentrated. The residue (yellow solid, 0.720 g) was purified by automated flash chromatography (SiO2, DCM/0-40% MeOH) to give the desired product (yellow solid, 0.347 g, 50%). HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=3.77 min, [M+H]+ m/z 276.1.

Workup

temperaturecooled to RT
washwashed with water
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue (yellow solid, 0.720 g) was purified by automated flash chromatography (SiO2, DCM/0-40% MeOH)

Sources & evidence

ORD record: ord-c538499f5f7948bd8e4dab435fa1478b
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815918B2

Reaction notes

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