(4-Chloro-2-fluorophenyl)boronic acid → HCID 86665940, Verbindung

HRID 63954

Reaktionsgleichung

Reaktionsgleichung von HRID 63954
[C:1]([O:5][C@@H:6]([C:11]1[C:12](I)=[C:13]2[C:20]3[CH2:21][CH2:22][CH2:23][CH2:24][C:19]=3[S:18][C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].[Cl:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[C:29]([F:36])[CH:28]=1>>[C:1]([O:5][C@@H:6]([C:11]1[C:12]([C:30]2[CH:31]=[CH:32][C:27]([Cl:26])=[CH:28][C:29]=2[F:36])=[C:13]2[C:20]3[CH2:21][CH2:22][CH2:23][CH2:24][C:19]=3[S:18][C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Komponenten

3

Edukt 2

HCID 4193595(4-Chloro-2-fluorophenyl)boronic acidHCID 69673123Methyl (2S)-tert-butoxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetate

Produkt 1

HCID 86665940HCID 86665940, Verbindung

Versuchsvorschrift

The title compound was prepared from Methyl (2S)-tert-butoxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetate (Preparation 16, 100 mg, 212 μmol) and (4-chloro-2-fluorophenyl) boronic acid (74 mg, 424 μmol) using the same method as described in Example 44, Step 1 to yield 57 mg, 56%. Material obtained was a mixture of atropisomers, in a 3:1 ratio. 1H NMR (400 MHz, CDCl3) δ ppm 1.01 (s, 9 H), 1.48-1.55 (m, 1 H), 1.69-1.75 (m, 3 H), 1.95-2.03 (m, 1 H), 2.72 (s, 3 H), 2.80-2.86 (m, 3 H), 3.66 (s, 3 H), 4.98 (s, 1 H), 7.19-7.21 (m, 1 H), 7.25-7.27 (m, 1 H), 7.35-7.37 (m, 1 H).

Aufarbeitung

  1. customto yield 57 mg, 56%
  2. customMaterial obtained
  3. additiona mixture of atropisomers

Quellen und Nachweise

ORD-Eintrag
ord-bce8d9803f87404e9af4934d28341406
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447116B2

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