Toluene → HCID 67170100, compound

HRID 1918344Notes

Reaction equation

HRID 1918344 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8](Br)[C:7]([O:11][CH3:12])=[N:6][CH:5]=1.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C(=O)(O)[O-].[Na+].C1(C)C=CC=CC=1>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.O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([C:15]([F:26])([F:25])[F:14])[CH:21]=2)[C:7]([O:11][CH3:12])=[N:6][CH:5]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 46311221Methyl 5-bromo-6-methoxypyridine-3-carboxylate

Product 1

HCID 67170100HCID 67170100, compoundYield 107.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

5-Bromo-6-methoxy-nicotinic acid methyl ester (1.03 g, 4.18 mmol), 3-trifluoromethylbenzeneboronic acid (0.795 g, 4.19 mmol), tetrakis(triphenylphosphine)palladium(0) (24 mg, 0.021 mmol) and sodium bicarbonate (1.05 g, 12.5 mmol) were partitioned between toluene (10 ml) and water (10 ml) under argon and stirred in reflux for 1 h. The material was partitioned between ethyl acetate and water, the combined organic extracts were dried over sodium chloride, filtered over a small plug of silica and evaporated to dryness. The solid material was titured with methanol, filtered and dried in vacuo to yield the title compound (1.4 g) sufficiently pure for further synthesis.

Workup

  1. temperaturein reflux for 1 h
  2. customThe material was partitioned between ethyl acetate and water
  3. dry with materialthe combined organic extracts were dried over sodium chloride
  4. filtrationfiltered over a small plug of silica
  5. customevaporated to dryness
  6. filtrationfiltered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-89eb0a37fbc14197ba98e656e1f7c387
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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