4-Chlorobenzoyl chloride → HCID 89514785, compound

HRID 527445Notes

Reaction equation

HRID 527445 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].CC([O-])(C)C.[Na+].[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1.[NH4+].[Cl-]>C1COCC1>[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[C:5]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:6]2[CH3:11])=[O:30])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 85014-Chlorobenzoyl chlorideHCID 25517Ammonium ChlorideHCID 23676156Sodium t-butoxideHCID 89514749HCID 89514749, compound

Product 1

HCID 89514785HCID 89514785, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution (ice bath, 0-5° C.) of methyl 3-(5-fluoro-2-methyl-1H-indol-3-yl)propanoate (80 mg, 0.34 mmol) in THF (2.5 mL) was added tBuONa (2 M in THF, 204 μL, 0.41 mmol), and the mixture was stirred for 20 min at the low temperature. 4-chlorobenzoyl chloride (71.4 mg, 0.41 mmol) was added and the reaction was stirred overnight at room temperature. The reaction was combined with saturated aqueous NH4Cl (1 mL; provided in a 10 mL glass vial) and the organic compound was extracted with ethyl acetate (3×3 mL), washed with brine and water, dried over Na2SO4 and concentrated in vacuo. The crude residue was subjected to flash chromatography (SiO2, ethyl acetate/hexane gradient) to afford the pure title compound as yellow oil in 49% yield (62 mg). C20H17ClFNO3, Mr=373.81; 1H NMR (400 MHz, DMSO-d6) d: 2.19 (s, 3H), 2.59 (t, J=7.4 Hz, 2H), 2.92 (t, J=7.6 Hz, 2H), 3.56 (s, 3H), 6.94 (td, J=2.4/9.2 Hz, 1H), 7.08 (dd, J=4.6/9.0 Hz, 1H), 7.39 (dd, J=2.4/9.2 Hz, 1H), 7.63-7.68 (m, 4H); LCMS (ESI) tR: 3.21 min (>95%, ELSD), m/z: 374.3 [M+1]+.

Workup

  1. stirringthe reaction was stirred overnight at room temperature

Sources & evidence

ORD record
ord-155899ee2ab949cc81d01f1a0bc09fa0
Source dataset
uspto-grants-2016_05
Patent number
US09346803B2

Reaction notes

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