Triphenylphosphine → HCID 73052132, compound

HRID 1048715Notes

Reaction equation

HRID 1048715 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:45]1([C:51]#[C:52][C:53]2[N:57]3[CH:58]=[CH:59][CH:60]=[CH:61][C:56]3=[N:55][C:54]=2[CH2:62]O)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>O1CCCC1>[C:45]1([C:51]#[C:52][C:53]2[N:57]3[CH:58]=[CH:59][CH:60]=[CH:61][C:56]3=[N:55][C:54]=2[CH2:62][O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 88068Methyl 3-Hydroxybenzoate2×HCID 5363146Diisopropyl azodicarboxylate2×HCID 90031842HCID 90031842, compound

Product 1

HCID 73052132HCID 73052132, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

0.09 g (0.594 mmol) of methyl 3-hydroxybenzoate were dissolved in 1 ml of tetrahydrofurane with magnetic stirring and then 0.312 g (1.188 mmol) of triphenylphosphine and 0.231 ml (1.188 mmol) of DIAD were added. The mixture was stirred at r.t. for 15 min and then a solution of 0.076 g (0.297 mmol) of (3-(phenylethynyl)imidazo[1,2-a]pyridin-2-yl)methanol in 4 ml of tetrahydrofurane was added and the mixture was stirred at r.t. for 16 h. A mixture of 0.09 g (0.594 mmol) of methyl 3-hydroxybenzoate, 0.312 g (1.188 mmol) of triphenylphosphine and 0.231 ml (1.188 mmol) of DIAD dissolved in 1 ml of tetrahydrofurane was added and the reaction medium was stirred at r.t. for a further 2 h. The reaction medium was treated with 10 ml. The aqueous phase was extracted with 3×10 ml of ethyl acetate and then the combined organic phases were washed with 10 ml of a saturated NaCl solution and then dried on Na2SO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo. The crude residue was purified by flash chromatography on a silica gel cartridge (eluent: heptane/ethyl acetate, from 70% to 40% heptane, v/v). 0.048 g (yield=42%) of methyl 3-((3-(phenylethynyl)imidazo[1,2-a]pyridin-2-yl)methoxy)benzoate were obtained as a pale yellow solid. LC-MS: m/z=383 (MH+); UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 8.64 (d, J=6.8 Hz, 1H), 7.68 (dd, J=17.0, 7.2 Hz, 4H), 7.55 (d, J=8.7 Hz, 1H), 7.52-7.34 (m, 6H), 7.15 (t, J=7.3 Hz, 1H), 5.42 (s, 2H), 3.80 (s, 3H).

Workup

  1. stirringThe mixture was stirred at r.t. for 15 min
  2. stirringthe mixture was stirred at r.t. for 16 h
  3. additionwas added
  4. stirringthe reaction medium was stirred at r.t. for a further 2 h
  5. additionThe reaction medium was treated with 10 ml
  6. extractionThe aqueous phase was extracted with 3×10 ml of ethyl acetate
  7. washthe combined organic phases were washed with 10 ml of a saturated NaCl solution
  8. customdried on Na2SO4 which
  9. customwas then removed by filtration
  10. concentrationThe obtained filtrate was concentrated in vacuo
  11. customThe crude residue was purified by flash chromatography on a silica gel cartridge (eluent: heptane/ethyl acetate, from 70% to 40% heptane, v/v)

Sources & evidence

ORD record
ord-574e887cfee64274a5438ecd3fb0bd77
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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