3,5-Bis-trifluoromethylphenylboronic acid → HCID 178508667, compound

HRID 855943Notes

Reaction equation

HRID 855943 reaction equation
I[C:2]1[C:3]2[NH:16][CH:15]=[CH:14][C:4]=2[C:5]2[C:10]([CH:11]=1)=[N:9][C:8]([NH2:12])=[N:7][C:6]=2[NH2:13].[F:17][C:18]([F:33])([F:32])[C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1.C(=O)(O)[O-].[Na+]>COCCOC.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:17][C:18]([F:32])([F:33])[C:19]1[CH:20]=[C:21]([C:2]2[C:3]3[NH:16][CH:15]=[CH:14][C:4]=3[C:5]3[C:10]([CH:11]=2)=[N:9][C:8]([NH2:12])=[N:7][C:6]=3[NH2:13])[CH:22]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:24]=1

Participants

7

Reactant 3

HCID 1562653,5-Bis-trifluoromethylphenylboronic acidHCID 516892Sodium BicarbonateHCID 178508676HCID 178508676, compound

Product 1

HCID 178508667HCID 178508667, compoundYield 53.5%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 6-iodo-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine (322 mg, 0.99 mmol) in ethylene glycol dimethyl ether (3.0 mL) and ethanol (3.0 mL)at 25° C. was treated with 3,5-bis(trifluoromethyl)benzene boronic acid (510 mg, 1.98 mmol), a saturated aqueous sodium bicarbonate solution (1.5 mL), and tetrakis(triphenylphosphine)-palladium (0) (115 mg, 0.1 mmol). The resulting mixture was heated to 80° C. for 18 h, cooled, filtered and the isolated solids washed with ethyl acetate. The filtrate was pre-absorbed onto silica gel and purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10/1 methylene chloride/methanol/ammonium hydroxide) to give 6-(3,5-bis-trifluoromethyl-phenyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine (218 mg, 53.5%) as a yellow solid; EI-HRMS m/e calcd for C18H11F6N5 (M+) 411.0918. Found 411.0921.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washthe isolated solids washed with ethyl acetate
  4. customThe filtrate was pre-absorbed onto silica gel
  5. custompurified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10/1 methylene chloride/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-16ef8f855ad04555aa1b5d4386b21960
Source dataset
uspto-grants-2007_08
Patent number
US07262297B2

Reaction notes

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