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

HRID 2409528
Notes
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Reaction equation

HRID 2409528 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27347023,4-Dimethoxyphenylboronic acidHCID 153575782-Bromo-6-methylimidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 667171682-(3,4-Dimethoxyphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazoleYield 50%

Reagents, catalysts & solvents 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 6344DichloromethaneSolvent2×
HCID 80711,2-DimethoxyethaneSolvent

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

  1. temperaturecooled to RT
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes