Cesium fluoride → (1-Methyl-8-phenyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester

HRID 48336Notes

Reaction equation

[CH2:1]([O:3][P:4]([CH:9]=[C:10]1[NH:16][CH2:15][CH2:14][N:13]([CH3:17])[C:12]2[CH:18]=[C:19](Cl)[CH:20]=[CH:21][C:11]1=2)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[F-].[Cs+]>O1CCOCC1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[CH2:1]([O:3][P:4]([CH:9]=[C:10]1[NH:16][CH2:15][CH2:14][N:13]([CH3:17])[C:12]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=[CH:21][C:11]1=2)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To 286 mg (0.83 mmol) of (8-chloro-1-methyl-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester (prepared as described in Example 48) in 1 ml of dioxane was added 106 mg (0.87 mmol) of phenylboronic acid, 8.4 mg (0.03 mmol) of tricyclohexylphosphine, 11.5 mg 0.013 mmol)of tris-(dibenzylideneacetone)-palladium (0) and 152 mg of caesium fluoride. The mixture was heated at 80° C. for 14 hours. The mixture was purified by column chromatography (20 g IST pre-packed column) eluting with acetone—petroleum ether (40-60° C.) (1:2) to give 227 mg of (1-methyl-8-phenyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester as a yellow oil; MS: m/e 387 [M+H]+.

Workup

customThe mixture was purified by column chromatography (20 g IST pre-packed column)
washeluting with acetone—petroleum ether (40-60° C.) (1:2)

Sources & evidence

ORD record: ord-c9ea94e3531743389edf6704a6819b23
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06703387B2

Reaction notes

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