Sodium Carbonate → HCID 86667784, compound

HRID 2400269Notes

Reaction equation

HRID 2400269 reaction equation
Cl[C:2]1[N:11]=[C:10]([CH2:12][CH2:13][NH2:14])[C:9]2[C:4](=[CH:5][C:6]([C:15]([F:18])([F:17])[F:16])=[CH:7][CH:8]=2)[N:3]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.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>[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24]([C:2]2[N:11]=[C:10]([CH2:12][CH2:13][NH2:14])[C:9]3[C:4](=[CH:5][C:6]([C:15]([F:18])([F:17])[F:16])=[CH:7][CH:8]=3)[N:3]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 86667783HCID 86667783, compound

Product 1

HCID 86667784HCID 86667784, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

A solution of (2-chloro-7-trifluoromethyl-quinazolin-4-yl)ethylamine (276 mg, 1.00 mmol), p-trifluoromethylphenylboronic acid (285 mg, 1.50 mmol), tetrakis(triphenylphosphine)palladium (116 mg, 0.10 mmol) and sodium carbonate (0.21 g, 2.0 mmol) in dimethoxyethane/water (3 mL, 2:1) was heated at 80° C. for 16 h. The reaction mixture was then concentrated under reduced pressure, diluted with water (50 mL) and extracted with CH2Cl2 (3×25 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by flash chromatography using cyclohexane:ethyl acetate (4:1) as solvent afforded [2-(4-trifluoromethylphenyl)-7-trifluoromethyl-quinazolin-4-yl]ethylamine. Yield=0.20 g, 52%; LC-MS: 3.2 min, 385 (M+); 1H NMR (DMSO-d6): δ 1.34 (t, 3 H, J=7.2 Hz), 3.68-3-78 (m, 2 H), 7.82 (dd, 1 H, J=8.6, 1.7 Hz), 7.88 (d, 2 H, J=8.1 Hz), 8.07 (s, 1 H), 8.50 (d, 1 H, J=8.6 Hz), 8.67 (d, 2 H, J=8.1 Hz), 8.70-8.76 (m, 1 H).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additiondiluted with water (50 mL)
  3. extractionextracted with CH2Cl2 (3×25 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-be1f963e920840bf9d06f58567e3475b
Source dataset
uspto-grants-2014_08
Patent number
US08796180B2

Reaction notes

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