Ammonium Chloride → HCID 89580780, compound

HRID 573425Notes

Reaction equation

HRID 573425 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.C([Li])CCC.[Br:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[C:24]([F:30])[CH:23]=1.[Cl-].[NH4+]>C1COCC1>[Br:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)[OH:27])=[C:24]([F:30])[CH:23]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 161127194-Bromo-6,7-dimethoxyquinolineHCID 178418339Butyllithium

Product 1

HCID 89580780HCID 89580780, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-bromo-6,7-dimethoxyquinoline (1.0 g, 3.73 mmol) in dry THF (20 mL) was cooled to −78° C. A solution of 2.5M n-butyllithium in hexanes (1.50 mL, 3.73 mmol) was added and stirred 15 min. A solution of 4-bromo-2-fluoro-benzaldehyde (0.757 g, 3.73 mmol) in THF (10 mL) was added dropwise over 5 min. After stirring 30 min. at −78° C., saturated ammonium chloride solution (1 mL) was added. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with water. After the solvent was removed under vacuum, the residue was purified by chromatography with 0-5% MeOH in dichloromethane to give (4-bromo-2-fluoro-phenyl)-(6,7-dimethoxy-quinolin-4-yl)-methanol in 52% yield. 1H NMR (CDCl3) δ: 8.63 (d, 1H, J=4.1 Hz), 7.57 (d, 1H, J=4.7 Hz), 7.34 (s, 1H), 7.25-7.17 (m, 2H), 7.08 (s, 1H), 6.67 (s, 1H), 4.02-3.96 (m, 1H), 3.94 (s, 3H), 3.88 (s, 3H).

Workup

  1. stirringAfter stirring 30 min. at −78° C.
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. customAfter the solvent was removed under vacuum
  6. customthe residue was purified by chromatography with 0-5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-59b307ee9d7f4f0b8db14b4789829d46
Source dataset
uspto-grants-2015_05
Patent number
US09029538B2

Reaction notes

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