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Water → HCID 59277773, compound

HRID 985507
Notes
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Reaction equation

HRID 985507 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]2=[N:4][CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.O>COCCOC.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>[NH2:12][C:13]1[CH:18]=[C:17]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]3=[N:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 922693-Aminophenylboronic acidHCID 167404763-Bromo-7-methylimidazo[1,2-a]pyridine

Product 1

HCID 59277773HCID 59277773, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 8071
1,2-Dimethoxyethane
Solvent

Procedure

3-Bromo-7-methylimidazo[1,2-α]pyridine (4.2 g, 20.0 mmol) and 3-aminophenylboronic acid (4.0 g, 25.8 mmol) were suspended in 1,2-dimethoxyethane (80 ml) and sodium carbonate (40 ml of a 2M solution) and the resulting solution degassed for 25 minutes. Tetrakis(triphenylphosphine)palladium(0) (250 mg, 0.2 mmol) was added and the mixture heated at reflux for 17 hours. The cooled reaction mixture was poured into water (150 ml), extracted with ethyl acetate (3×70 ml) and the combined organics dried over anhydrous magnesium sulphate. The solution was filtered and concentrated in vacuo to yield 3-(3-aminophenyl)-7-methylimidazo[1,2-α]pyridine as a colourless oil (4.5 g, 100%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δH 2.38 (3H, s), 3.58 (2H, br s), 6.60 (1H, d, J 7), 6.70 (1H, d, J 8), 6.81 (1H, s), 6.91 (1H, d, J8), 7.24-7.28 (1H, m), 7.39 (1H, s), 7.57 (1H, s), 8.23 (1H, d, J 7); m/z (ES+) 224 (M++H).

Workup

  1. customsodium carbonate (40 ml of a 2M solution) and the resulting solution degassed for 25 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux for 17 hours
  4. customThe cooled reaction mixture
  5. extractionextracted with ethyl acetate (3×70 ml)
  6. dry with materialthe combined organics dried over anhydrous magnesium sulphate
  7. filtrationThe solution was filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c451b66b838456aa713b6a15d043c2a
Source dataset
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06872731B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes