Water → HCID 46881404, compound

HRID 1253911Notes

Reaction equation

HRID 1253911 reaction equation
O=P(Cl)(Cl)Cl.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=3)[C:19]([O:21]C)=[O:20])[CH:13]=2)[CH:8]=[CH:7]1.O.CN([CH:30]=[O:31])C>>[CH:30]([C:8]1[C:9]2[C:14](=[CH:13][C:12]([CH2:15][C:16]3[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=3)[C:19]([OH:21])=[O:20])=[CH:11][CH:10]=2)[NH:6][CH:7]=1)=[O:31]

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 58381091HCID 58381091, compound

Product 1

HCID 46881404HCID 46881404, compound

Conditions

Temperature
40 °C

Procedure

(I-8): 3 ml anhydrous DMF was cooled in ice-water bath, then 50 μl POCl3 was added, the solution was stirred about 15 minutes, then 32 mg of methyl 3-(1H-indol-6-ylmethyl)benzoate in 2 ml DMF was added. The mixture was heated to 40° C. for 3 hours. After cooling to room temperature, the mixture was treated by cold water, following the general procedure above, the target compound was purified as a brown solid. Mass calculated for C17H13NO3: 279; LCMS: 280.6 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.87 (1H, s), 8.24 (1H, d, J=3.0 Hz), 7.99 (1H, s), 7.80 (1H, d, J=7.3 Hz), 7.76 (1H, d, J=7.9 Hz), 7.52 (1H, d, J=7.9 Hz), 7.41 (1H, t, J=7.9 Hz), 7.34 (1H, s), 7.12 (1H, d, J=7.3 Hz), 4.12 (2H, s).

Workup

  1. temperatureAfter cooling to room temperature
  2. customwas purified as a brown solid

Sources & evidence

ORD record
ord-3827707b6e834cda9b2c3449b7c84945
Source dataset
uspto-grants-2013_06
Patent number
US08455516B2

Reaction notes

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