Water → HCID 57827398, compound

HRID 1842171Notes

Reaction equation

HRID 1842171 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C(O[Na])(C)(C)C.[C:15]([O:19][C:20]([N:22]([C:30]1[S:31][CH2:32][C@@H:33]2[CH2:38][CH2:37][CH2:36][C@:34]2([C:39]2[CH:44]=[C:43]([NH2:45])[CH:42]=[CH:41][C:40]=2[F:46])[N:35]=1)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:21])([CH3:18])([CH3:17])[CH3:16].O>C1(C)C=CC=CC=1.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:15]([O:19][C:20]([N:22]([C:30]1[S:31][CH2:32][C@@H:33]2[CH2:38][CH2:37][CH2:36][C@:34]2([C:39]2[CH:44]=[C:43]([NH:45][C:2]3[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=3)[CH:42]=[CH:41][C:40]=2[F:46])[N:35]=1)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:21])([CH3:16])([CH3:17])[CH3:18]

Participants

8

Reactant 4

HCID 962WaterHCID 8170982-Bromo-5-chloropyridineHCID 57827297HCID 57827297, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 57827398HCID 57827398, compoundYield 200.1%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-5-chloropyridine (10 mg), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (4.86 mg), tris(dibenzylideneacetone)dipalladium (0) (2.38 mg) and tert-butoxysodium (6.5 mg) were added to a solution of (±)-di-tert-butyl[(4aR*,7aS*)-7a-(5-amino-2-fluorophenyl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl]imidodicarbonate (29.1 mg) in toluene (10 mL). The mixture was heated with stirring under a nitrogen atmosphere at 100° C. for five hours. The reaction solution was returned to room temperature and poured into water, followed by extraction with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. The title compound (60 mg) was obtained by removal of the drying agent and concentration under reduced pressure.

Workup

  1. temperatureThe mixture was heated
  2. customwas returned to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-beb39d2d5ca14bc58a1b8d50c7030761
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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