p-Acetamidobenzoic acid → 4-Acetylamino-N-[2-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide

HRID 252828

Reaktionsgleichung

Reaktionsgleichung von HRID 252828
[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[CH:11][C:12]([N+:16]([O-:18])=[O:17])=[C:13]([NH2:15])[CH:14]=2)[O:3]1.[C:20]([NH:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)(=[O:22])[CH3:21].C(NC1C=CC(C(O)=O)=CC=1)(=O)C>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:20]([NH:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:15][C:13]2[CH:14]=[C:9]([B:4]3[O:3][C:2]([CH3:19])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)[CH:10]=[CH:11][C:12]=2[N+:16]([O-:18])=[O:17])=[O:29])=[CH:26][CH:25]=1)(=[O:22])[CH3:21]

Komponenten

6

Edukt 3

HCID 19266p-Acetamidobenzoic acidHCID 70103414-Acetamidobenzoyl chlorideHCID 597369762-Nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Produkt 1

HCID 597367494-Acetylamino-N-[2-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamideAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of compound 132 (18 mg, 0.689 mmol) in pyridine (2.8 mL) was added 4-acetamidobenzoyl chloride (150 mg, 0.758 mmol) and 4-(dimethylamino)pyridine (8 mg, 0.07 mmol) and the mixture was stirred for 16 h. at r.t. Then, it was partitioned between EtOAc and H2O, The aqueous layer was extracted with fresh EtOAc and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting crude oil was purified by flash chromatography on silica gel using methanol/EtOAc (5:95) as the eluent affording the title compound 133 (47 mg, 16% yield) as a 1:1 mixture with 4-acetamidobenzoic acid (hydrolyzed starting material). 1H NMR: (Acetone-d6) δ(ppm): 10.76 (bs, 1H), 9.52 (bs, 1H), 9.00 (d, J=1.0 Hz, 1H), 8.20 (d, J=7.2 Hz, 1H), 7.99 (d, J=8.6 Hz, 2H), 7.85 (d, J=8.6 Hz, 2H), 7.64 (dd, J=8.2, 1.2 Hz, 1H), 2.15 (s, 3H), 1.40 (s, 12H).

Aufarbeitung

  1. customThen, it was partitioned between EtOAc and H2O
  2. extractionThe aqueous layer was extracted with fresh EtOAc
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude oil was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f3ebc4f6d88642c18ad4ee41ff658ec1
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868205B2

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