Benzene, 1-iodo-3-methoxy- → HCID 66748666, compound

HRID 1405927Notes

Reaction equation

HRID 1405927 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[NH2:10][C:11]1[C:16]([C:17]2[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=2)=[CH:15][CH:14]=[CH:13][N:12]=1.O.O.O.O.O.O.O.O.O.O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1COCC1.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>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([C:20]2[CH:19]=[CH:18][C:17]([C:16]3[C:11]([NH2:10])=[N:12][CH:13]=[CH:14][CH:15]=3)=[CH:22][CH:21]=2)[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 3

HCID 69839Benzene, 1-iodo-3-methoxy-HCID 151402Sodium Carbonate DecahydrateHCID 66747940HCID 66747940, compound

Product 1

HCID 66748666HCID 66748666, compoundYield 72.6%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (8.49 mg) was added to a suspension of 1-iodo-3-methoxybenzene (68.8 mg), 4-(2-aminopyridin-3-yl)phenylboronic acid (52.4 mg) and sodium carbonate decahydrate (210 mg) in DME (5 mL), water (1 mL) and THF (dry) (5 mL). The mixture was stirred at 80° C. under nitrogen overnight. Silica-gel was added and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane) to give the title compound (49.1 mg) as a white solid.

Workup

  1. additionSilica-gel was added
  2. customthe volatiles were removed in vacuo
  3. customwas purified by column chromatography (NH silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-6e26ef61798b456fa3db5bda8000b5d2
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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