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Pyridine → N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxamide

HRID 888428
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 888428
[CH3:1][C:2]1[C:7]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:17].N1C=CC=CC=1.[S:24]1[C:28]([C:29](Cl)=[O:30])=[CH:27][C:26]2[CH2:32][CH2:33][CH2:34][CH2:35][C:25]1=2>C(Cl)Cl>[CH3:1][C:2]1[C:7]([B:8]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH3:16])([CH3:15])[O:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:17][C:29]([C:28]1[S:24][C:25]2[CH2:35][CH2:34][CH2:33][CH2:32][C:26]=2[CH:27]=1)=[O:30]
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Komponenten

5

Edukt 3

HCID 1049PyridineHCID 64853624,5,6,7-Tetrahydro-benzo[b]thiophene-2-carbonyl chlorideHCID 467380052-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Produkt 1

HCID 58729134N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxamideAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

2-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (7) (1.20 g, 5.16 mmol, 1.0 equiv) and pyridine (0.42 mL, 25.8 mmol) are dissolved in DCM (40 mL) at 0° C. under a nitrogen atmosphere. 4,5,6,7-Tetrahydro-benzo[b]thiophene-2-carbonyl chloride (8) (1.03 g, 5.16 mmol) is then added in portions over 5 min and allowed to react warming to RT over 60 min. All solvent is then removed under reduced pressure, and the resultant oil is reduced from toluene (3×20 mL) to remove residual pyridine. The residue is then dissolved in ethyl acetate and washed with sodium hydroxide (1N, 1×100 mL), then washed with saturated sodium chloride (1×100 mL) and dried over sodium sulfate. The solution is then filtered and concentrated under reduced pressure to give 4,5,6,7-tetrahydro-benzo[b]thiophene-2-carboxylic acid [2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]diaxaborolan-2-yl)-phenyl]-amide (9) as an off-white solid (1.87 g).

Aufarbeitung

  1. customto react
  2. customAll solvent is then removed under reduced pressure
  3. customto remove residual pyridine
  4. dissolutionThe residue is then dissolved in ethyl acetate
  5. washwashed with sodium hydroxide (1N, 1×100 mL)
  6. washwashed with saturated sodium chloride (1×100 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationThe solution is then filtered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5a08ce3daf9b445f80492ad19929f23c
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08247550B2

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