Triethyl phosphite → HCID 22720011, compound

HRID 1582228Notes

Reaction equation

[P:1]([O:8][CH2:9][CH3:10])([O:5]CC)[O:2][CH2:3][CH3:4].Br[CH2:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:19]2[CH3:22])=[C:15]([C:28]([F:31])([F:30])[F:29])[CH:14]=1>>[CH2:9]([O:8][P:1]([CH2:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:19]2[CH3:22])=[C:15]([C:28]([F:31])([F:30])[F:29])[CH:14]=1)([O:2][CH2:3][CH3:4])=[O:5])[CH3:10]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 22719999HCID 22719999, compound

Product 1

HCID 22720011HCID 22720011, compoundYield 95.3%

Conditions

Temperature: 140 °C

Procedure

Under nitrogen, triethyl phosphite (589 μl, 3.43 mmol) was added to ethyl 6-(bromomethyl)-1-methyl-4-(trifluoromethyl)-1H-indole-2-carboxylate (250 mg, 0.687 mmol), and the resulting mixture was stirred for 2 hours while being maintained at 140° C. The excess triethyl phosphite was distilled off as much as possible, and the resulting concentrated residue was purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=15/1, 10/1, 3/1, 1/1, 1/4 and 0/10) to obtain 276 mg of ethyl 6-[(diethoxyphosphoryl)methyl]-1-methyl-4-(trifluoromethyl)-1H-indole-2-carboxylate as a white solid.

Workup

distillationThe excess triethyl phosphite was distilled off as much as possible, and the resulting concentrated residue
customwas purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=15/1, 10/1, 3/1, 1/1, 1/4 and 0/10)

Sources & evidence

ORD record: ord-586fe6a6be764715985add5eb70af86c
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734205B2

Reaction notes

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