Ammonia → 1-(4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromophenyl)methanamine

HRID 2172534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2172534
CS(Cl)(=O)=O.[F:6][C:7]([F:37])([F:36])[C:8]1[CH:13]=[C:12]([C:14]2([C:28]([F:31])([F:30])[F:29])[CH2:18][C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25]O)=[C:21]([Br:27])[CH:20]=3)=[N:16][CH2:15]2)[CH:11]=[C:10]([C:32]([F:35])([F:34])[F:33])[N:9]=1.C([N:40](CC)CC)C.N>C1COCC1.CO>[F:6][C:7]([F:37])([F:36])[C:8]1[CH:13]=[C:12]([C:14]2([C:28]([F:31])([F:30])[F:29])[CH2:18][C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][NH2:40])=[C:21]([Br:27])[CH:20]=3)=[N:16][CH2:15]2)[CH:11]=[C:10]([C:32]([F:35])([F:34])[F:33])[N:9]=1

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86664623(4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromophenyl)methanol

Produkt 1

HCID 866646241-(4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromophenyl)methanamineAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Methanesulfonyl chloride (0.17 g) was added to (4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromophenyl)methanol (0.46 g) and triethylamine (0.26 g) in THF at −10° C. and the resultant mixture was stirred for 30 min. The mixture was poured into ammonia (10 ml), THF (10 ml) and MeOH (10 ml), and the resultant was stirred at room temperature overnight. After the solvents were evaporated under reduced pressure, the residue was diluted with t-BuOMe and H2O, and the organic layer was dried over MgSO4. After the solvents were evaporated under reduced pressure, the residue was purified with column chromatography to get the targeted product (0.4 g).

Aufarbeitung

  1. customAfter the solvents were evaporated under reduced pressure
  2. additionthe residue was diluted with t-BuOMe and H2O
  3. dry with materialthe organic layer was dried over MgSO4
  4. customAfter the solvents were evaporated under reduced pressure
  5. customthe residue was purified with column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8574e523e31747c5810747865c8846af
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09055749B2

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