Triphenyl[(pyridin-2-yl)methyl]phosphanium chloride--hydrogen chloride (1/1/1) → HCID 50915291, compound

HRID 1191325Notes

Reaction equation

HRID 1191325 reaction equation
Cl.[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)C=CC=CC=1.C([Li])CCC.[Br:34][C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[NH:41][C:40](=[O:45])[C:39]([C:46]1[S:47][CH:48]=[CH:49][CH:50]=1)=[C:38]2[CH:51]=O>O1CCCC1>[Br:34][C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[NH:41][C:40](=[O:45])[C:39]([C:46]1[S:47][CH:48]=[CH:49][CH:50]=1)=[C:38]2/[CH:51]=[CH:10]/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 16213046Triphenyl[(pyridin-2-yl)methyl]phosphanium chloride--hydrogen chloride (1/1/1)HCID 77231106HCID 77231106, compoundHCID 178418339Butyllithium

Product 1

HCID 50915291HCID 50915291, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution containing triphenyl(2-pyridylmethyl)phosphonium chloride hydrochloride (153 mg, 0.359 mmol) in tetrahydrofuran (2.26 ml) at −78° C. was added n-butyl lithium (2.50 M, 0.685 mmol). This mixture was stirred for 15 min. and then added to a solution containing 6-bromo-2-oxo-3-(thiophen-2-yl)-1,2-dihydroquinoline-4-carbaldehyde (109 mg, 0.326 mmol) in tetrahydrofuran (1 ml) at −78° C. The reaction was allowed to stir for 4 h at room temperature. The reaction was quenched with 1 N hydrochloric acid (10 ml) and then the pH was increased with 1 N sodium hydroxide. This mixture was extracted with ethyl acetate (3×30 ml). The organic layers were combined and extracted with sodium chloride (1×25 ml). The organic layer was then dried over magnesium sulfate, filtered and concentrated. The resulting crude solid was purified by reverse phase chromatography to afford 6-bromo-4-[(E)-2-(pyridine-2-yl)ethenyl]-3-(thiophen-2-yl)quinolin-2(1H)-one as a yellow solid. LCMS (M+H)=410.69. 1H NMR (400 MHz, d6-DMSO) δ 12.28 (s, 1H), 8.63-8.60 (m, 1H), 7.95 (d, 1H), 7.85 (m, 1H), 7.74-7.65 (m, 3H), 7.60 (d, 1H), 7.39-7.33 (m, 3H), 7.09 (dd, 1H), 6.99 (d, 1H).

Workup

  1. additionadded to a solution
  2. stirringto stir for 4 h at room temperature
  3. customThe reaction was quenched with 1 N hydrochloric acid (10 ml)
  4. temperaturethe pH was increased with 1 N sodium hydroxide
  5. extractionThis mixture was extracted with ethyl acetate (3×30 ml)
  6. extractionextracted with sodium chloride (1×25 ml)
  7. dry with materialThe organic layer was then dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting crude solid was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-8eabbc8c86b84c2ca645594f410593bb
Source dataset
uspto-grants-2014_03
Patent number
US08680116B2

Reaction notes

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