Water → HCID 57827398, compound

HRID 1693254Notes

Reaction equation

HRID 1693254 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-22cb3877ddd04499b4a286704f89954f
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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