Water → HCID 60164618, compound

HRID 1771068Notes

Reaction equation

HRID 1771068 reaction equation
[N:1]1([CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15](OC)=[O:16])=[CH:13][CH:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[NH4+:22].O>CO>[N:1]1([CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([NH2:22])=[O:16])=[CH:13][CH:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 3399806HCID 3399806, compound

Product 1

HCID 60164618HCID 60164618, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-((1H-indol-1-yl)methyl)benzoate 1 was dissolved in MeOH (10 mL) and to it was added a 30% solution of ammonium hydroxide (5 mL). The reaction was heated to reflux for 16 h after which it was cooled to RT and H2O (30 mL) was added. The organic products were extracted with EtOAc (3×15 mL), washed with brine (15 mL), dried with Na2SO4 and concentrated in vacuo. The crude product was dissolved in DMF and purified by preparatory HPLC method 1. The title compound was isolated as a white solid (37 mg, 13%). 1H NMR (400 MHz, MeOD): δ 7.79 (d, J=7.9 Hz, 2H), 7.58 (d, J=7.8 Hz, 1H), 7.29 (m, 2H), 7.19 (d, J=8.0 Hz, 2H), 7.11 (t, J=7.2 Hz, 1H), 7.04 (t, J=7.5 Hz, 1H), 6.53 (d, J=2.8 Hz, 1H), 5.47 (s, 2H). 13C NMR (100 MHz, MeOD): δ 170.59, 142.41, 136.24, 132.64, 128.93, 128.14, 127.57, 126.36, 121.13, 120.32, 118.99, 109.29, 101.14, 48.93. ESI-LRMS: [M+H]+=251.1 m/z. ESI-HRMS: calc. for C16H14N2O: [M+H]+=251.1179 m/z, found: [M+H]+=251.1179 m/z.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 16 h after which it
  3. extractionThe organic products were extracted with EtOAc (3×15 mL)
  4. washwashed with brine (15 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated in vacuo
  7. dissolutionThe crude product was dissolved in DMF
  8. custompurified by preparatory HPLC method 1

Sources & evidence

ORD record
ord-218868ae8cad4ab4bd2b92c98fed4d67
Source dataset
uspto-grants-2016_02
Patent number
US09249087B2

Reaction notes

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