Phenyl ethenesulfonate → 1-Methyl-4-(vinylsulfonyl)piperazine

HRID 272552

Reaction equation

C1C2[C:10]3=[CH:12]C4C=CC(C(O)=O)=[CH:17][C:18]=4[N:9]3[CH2:8]C=CC=2C=CC=1.C1(C2C3C(=CC(C([O-])=O)=CC=3)[NH:30]C=2C2C=CC(OC)=CC=2C=O)CCCCC1.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[CH:68]([S:70]([O:73]C1C=CC=CC=1)(=O)=[O:71])=[CH2:69]>O1CCOCC1>[CH3:8][N:9]1[CH2:10][CH2:12][N:30]([S:70]([CH:68]=[CH2:69])(=[O:73])=[O:71])[CH2:17][CH2:18]1

Participants

Conditions

Temperature: 22 °C

Procedure

7H-Indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-methoxy-6-(phenoxysulfonyl)-,1,1-dimethylethyl ester. To a solution of tbutyl 3-cyclohexyl-2-(2-formyl-4-methoxyphenyl)-1H-indole-6-carboxylate (4.40 g, 11.2 mmol) in dioxane (30.0 mL) and BEMP (4.88 mL, 16.9 mmol) was added phenyl vinylsulfonate (4.14 g, 22.5 mmol). The resulting mixture was stirred at 22° C. for 1 hr and then at 110° C. in a sealed tube in a microwave for 15 min. The resulting mixture was concentrated under reduced pressure. Silica gel chromatography (1:1 EtOAc:hexanes) of the concentrate afforded the title compound (3.49 g, 52%) as a yellow oil. MS m/z 600 (MH+), ret time 3.11 min, column B, 4 minute gradient, flow rate 4 mL/min.

Workup

waitat 110° C. in a sealed tube in a microwave for 15 min
concentrationThe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-a280fb2a30fa4f82a578fd6d00456f67
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456167B2

Linked notes

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