Oxalyl chloride → 2-(1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)acetyl chloride

HRID 527449Notes

Reaction equation

HRID 527449 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Cl:7][C:8]1[CH:30]=[CH:29][C:11]([C:12]([N:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][CH:21]=3)[C:16](CC(O)=O)=[CH:15]2)=[O:13])=[CH:10][CH:9]=1>C(Cl)Cl>[Cl:7][C:8]1[CH:30]=[CH:29][C:11]([C:12]([N:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][CH:21]=3)[C:16]([CH2:1][C:2]([Cl:4])=[O:3])=[CH:15]2)=[O:13])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 47116971-(4-chlorobenzoyl)-5-methoxy-1H-indole-3-acetic acid

Product 1

HCID 716012132-(1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)acetyl chlorideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (30 μL, 0.35 mmol) was added dropwise to a solution of 2-(1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)acetic acid (100 mg, 0.29 mmol) in 2 mL of dry CH2Cl2 under argon. The reaction mixture was stirred overnight at room temperature. The solvent was evaporated and the crude product was washed with dry hexane (3×1 mL) and dried in vacuo to give the title compound in 95% yield (100 mg). C18H13Cl2NO3, Mr=362.21; 1H NMR (400 MHz, DMSO-d6) d: 3.90 (s, 3H), 4.21 (s, 2H), 6.95 (d, J=2.4 Hz, 1H), 7.04 (dd, J=2.4/9.0 Hz, 1H), 7.29 (s, 1H), 7.52-7.55 (m, 2H), 7.67-7.71 (m, 2H), 8.29 (d, J=9.2 Hz, 1H); LCMS (ESI) tR: 2.72 min (>99%, UV254), m/z: 358.2 [M+1]+.

Workup

  1. customThe solvent was evaporated
  2. washthe crude product was washed with dry hexane (3×1 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-cc44fd4583ec4b8e8f848001b67c11f6
Source dataset
uspto-grants-2016_05
Patent number
US09346803B2

Reaction notes

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