Cesium carbonate → HCID 178431684, compound

HRID 339903

Reaction equation

HRID 339903 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:19][C:20]1[O:21][C:22]([CH3:44])([CH3:43])[CH:23]([C:28]2[CH:33]=[CH:32][C:31](B3OC(C)(C)C(C)(C)O3)=[CH:30][CH:29]=2)[S:24](=[O:27])(=[O:26])[N:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:45]([N:49]1[CH2:54][CH:53]=[C:52](OS(C(F)(F)F)(=O)=O)[CH2:51][CH2:50]1)([CH3:48])([CH3:47])[CH3:46].C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.C1C=CC([C]2[C](C3C=CC=CC=3)[C](C3C=CC=CC=3)[C](C3C=CC=CC=3)[C]2C2C=CC=CC=2)=CC=1.[Fe].O1CCOCC1.O>[Si:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:19][C:20]1[O:21][C:22]([CH3:44])([CH3:43])[CH:23]([C:28]2[CH:29]=[CH:30][C:31]([C:52]3[CH2:51][CH2:50][N:49]([C:45]([CH3:46])([CH3:47])[CH3:48])[CH2:54][CH:53]=3)=[CH:32][CH:33]=2)[S:24](=[O:27])(=[O:26])[N:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 186942921-tert-Butyl-4-Trifluoromethanesulfonlyoxy-1,2,3,6-tetrahydropyridineHCID 178431682HCID 178431682, compound

Product 1

HCID 178431684HCID 178431684, compoundYield 67.8%

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 178454872HCID 178454872, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
62 °C

Procedure

To a solution of [(S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propyl]-{6,6-dimethyl-4,4-dioxo-5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-5,6-dihydro-4H-4lambda*6*-[1,4,3]oxathiazin-2-yl}amine (300 mg), trifluoromethanesulfonic acid 1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl ester (208 mg) and cesium carbonate (519 mg) in 3:1 dioxane/water (4 ml) were added Pd(dba)2 (31 mg) and CTC-Q-Phos (75 mg), and the mixture was stirred at 62° C. for 40 min. After dilution with ethyl acetate, the mixture was washed with water, dried using a kieselguhr cartridge and concentrated. This was followed by purification by column chromatography (ethyl acetate/heptane). This gave the product (207 mg) with a molecular weight of 658.0 g/mol (C35H52FN3O4SSi).

Workup

  1. washAfter dilution with ethyl acetate, the mixture was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customThis was followed by purification by column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-06d5ff6be70a409ebd1cd6a503bee4d9
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Linked notes

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