Water → HCID 59762957, compound

HRID 878796Notes

Reaction equation

HRID 878796 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][CH:14]=2.O.[CH3:24]CCCCC>C(Cl)Cl>[CH3:24][O:22][C:20]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:19]2[C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8058HexaneHCID 216222322-Methyl-1H-indole-5-carboxylic acid

Product 1

HCID 59762957HCID 59762957, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alluminium trichloride (0.550 g, 2.50 mmol, 2.2 eq) was added to a solution of benzoyl chloride (0.319 g, 2.274 mol, 2 eq) in anhydrous DCM (5 ml). After stirring at room temperature under Ar for 30 min, methyl 5-carboxy indole (0.199 g, 1.157 mmol) was added. After stirring for 2 h at room temperature, the reaction mixture was poured into water (5 ml). The product was extracted with DCM (3×10 ml). The organic extracts were collected, dried over Na2SO4 and the solvent removed under reduced pressure to afford a brown solid. The pure compound rpm123 was obtained after trituration with hexane (10 ml) as a off-whte solid (0.205 g, 0.737 mmol, 64%), mp 271-273° C. 1H (400 MHz, DMSO-d6) δ 3.87 (3H, s), 7.52-7.61 (4H, m), 7.79-7.31 (2H, m), 7.87 (1H, dd, J 1.4, 8.6 Hz), 8.08 (1H, d, J 3.2 Hz), 8.9 (1H, d, J 1.2 Hz), 12.36 (1H, s). 13C NMR (100 MHz, DMSO-d6) δ 190.64, 167.70, 140.74, 140.16, 138.34, 132.07, 129.19, 129.14, 126.61, 124.77, 124.51, 123.93, 116.30, 113.13, 52.61.

Workup

  1. stirringAfter stirring for 2 h at room temperature
  2. extractionThe product was extracted with DCM (3×10 ml)
  3. customThe organic extracts were collected
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed under reduced pressure
  6. customto afford a brown solid

Sources & evidence

ORD record
ord-96811552c6e74f93810d5b24381faaaf
Source dataset
uspto-grants-2015_03
Patent number
US08987474B2

Reaction notes

Loading…