Sodium methanesulfinate → tert-Butyl 2-(7-(3-Cyano-4-isopropoxybenzyloxy)-9-(methylsulfonyl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

HRID 1964155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1964155
[C:1]([C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[O:32][CH:33]([CH3:35])[CH3:34])[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH:19]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:12]3=[C:11](I)[C:10]=2[CH:9]=1)#[N:2].[CH3:36][S:37]([O-:39])=[O:38].[Na+]>CN1C(=O)CCC1.[Cu]I>[C:1]([C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[O:32][CH:33]([CH3:35])[CH3:34])[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH:19]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:12]3=[C:11]([S:37]([CH3:36])(=[O:39])=[O:38])[C:10]=2[CH:9]=1)#[N:2]

Komponenten

5

Edukt 2

HCID 2733271Sodium methanesulfinateHCID 86654873tert-Butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-9-iodo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Produkt 1

HCID 67250041tert-Butyl 2-(7-(3-Cyano-4-isopropoxybenzyloxy)-9-(methylsulfonyl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetateAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

tert-Butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-9-iodo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (100 mg, 0.171 mmol) in NMP (2 mL) was added copper(I) iodide (162 mg, 0.853 mmol) and sodium methanesulfinate (102 mg, 0.853 mmol). The reaction mixture was heated at 125° C. under nitrogen protection for 8 h. The solid was filtered and washed with ethyl acetate. The filtrate was washed with water and dried over anhydrous Na2SO4. The solvent was evaporated and the residue was purified by column chromatography to give the title compound (36 mg). LCMS m/z=539.6 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.36 (s, 9H), 1.40 (d, J=6.0 Hz, 6H), 2.46-2.55 (m, 1H), 2.74 (dd, J=16.0, 9.0 Hz, 1H), 2.88-2.98 (m, 1H), 3.12 (s, 3H), 3.08-3.14 (dd, J=16.0, 3.6 Hz, 1H), 3.95-4.02 (m, 1H), 4.05-4.20 (m, 2H), 4.62-4.69 (m, 1H), 5.03 (s, 2H), 6.95 (dd, J=8.8, 2.4 Hz, 1H), 6.98 (d, J=8.8 Hz, 1H), 7.20 (d, J=8.8 Hz, 1H), 7.41 (d, J=2.4 Hz, 1H), 7.59 (dd, J=8.7, 2.2 Hz, 1H), 7.65 (d, J=2.2 Hz, 1H).

Aufarbeitung

  1. filtrationThe solid was filtered
  2. washwashed with ethyl acetate
  3. washThe filtrate was washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated
  6. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b2aa5de6d08c4457a7b8495226bb9469
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415484B2

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