Indole-3-Carboxaldehyde → HCID 86673811, compound

HRID 1527190Notes

Reaction equation

HRID 1527190 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.[H-].[Na+].[CH2:14]([O:21][CH2:22][C:23](Cl)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([O:21][CH2:22][C:23]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10256Indole-3-CarboxaldehydeHCID 24758Sodium hydride2×HCID 177085Benzyloxyacetyl chloride2×

Product 1

HCID 86673811HCID 86673811, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of indole-3-carboxaldehyde (2 g, 13.8 mmol) in THF (70 mL) at 5° C., was added NaH (60% in mineral oil, 551 mg, 13.8 mmol) under nitrogen atmosphere. The mixture was stirred at 5° C. for 30 min before dropwise addition of benzyloxyacetyl chloride (2.6 mL, 16.53 mmol) over 20 min maintaining the internal temperature between 5° C. and 10° C. The resulting dark solution was further stirred at RT for 1 h. As the reaction was not completed benzyloxyacetyl chloride (1 mL, 6.44 mmol, 0.5 eq) and NaH (60% in mineral oil, 551 mg, 13.8 mmol) were added and the mixture was further stirred at RT for 3 days. The reaction mixture was concentrated, and the residue taken up in CH2Cl2 and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated. The crude material was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 4-1) corresponding to the desired compound. TLC, Rf (c-hexane/EtOAc 1:1)=0.61; MS (LC/MS): 294.1 [M+H]+, 316.1 [M+Na]+; tR (HPLC conditions a): 3.87 min.

Workup

  1. temperaturemaintaining the internal temperature between 5° C. and 10° C
  2. additionwere added
  3. stirringthe mixture was further stirred at RT for 3 days
  4. concentrationThe reaction mixture was concentrated
  5. washwashed with water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 4-1) corresponding to the desired compound
  10. custom3.87 min.

Sources & evidence

ORD record
ord-47f74d0944a74dfba9c60e5ae34771a0
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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