Triethylamine → HCID 68294609, compound

HRID 1850069Notes

Reaction equation

HRID 1850069 reaction equation
[NH:1]1[CH2:4][C:3](=[CH:5][C:6]2[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=2[Cl:16])[CH2:2]1.C(N(CC)CC)C.[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([CH:33]=O)[CH:31]=2)[CH:26]=[CH:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C(Cl)Cl.C(Cl)Cl>[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([CH2:33][N:1]3[CH2:4][C:3](=[CH:5][C:6]4[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=4[Cl:16])[CH2:2]3)[CH:31]=2)[CH:26]=[CH:25]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27734351H-Indole-6-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68294015HCID 68294015, compound

Product 1

HCID 68294609HCID 68294609, compoundYield 112%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A solution of the hydrochloride salt of methyl 4-(azetidin-3-ylidenemethyl)-3-chlorobenzoate (0.20 g, 0.73 mmol) in THF:DCM (2:1) (25 mL) was neutralized by addition of triethylamine (0.14 mL, 0.88 mmol). After stirring at room temperature for 20 mins, indole-6-carboxaldehyde (0.16 g, 1.00 mmol) and sodium triacetoxyborohydride (0.50 g, 2.37 mmol) were added and the reaction mixture was heated at 50° C. overnight. It was then diluted with DCM (50 mL) and washed with saturated sodium bicarbonate (3×25 mL) and brine (1×15 mL). The organic layer was separated, dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum to give the crude product which was purified by silica gel column chromatography using 10-40% EtOAc in hexanes as eluent. Fractions containing the pure product were pooled and evaporated to give 0.3 g of methyl 4-((1-((1H-indol-6-yl)methyl)azetidin-3-ylidene)methyl)-3-chlorobenzoate (0.30 g) as a colorless oil. ES+(M+H)+367

Workup

  1. temperaturethe reaction mixture was heated at 50° C. overnight
  2. washwashed with saturated sodium bicarbonate (3×25 mL) and brine (1×15 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum
  7. customto give the crude product which
  8. customwas purified by silica gel column chromatography
  9. additionFractions containing the pure product
  10. customevaporated

Sources & evidence

ORD record
ord-e03e205ef80549e7a4d0d560ee1206bc
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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