Sodium Carbonate → HCID 57827644, compound

HRID 1693256Notes

Reaction equation

HRID 1693256 reaction equation
[F:1][C:2]1[C:7](B(O)O)=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OC([N:24]([C:29]1[S:30][CH2:31][C@@H:32]2[CH2:37][CH2:36][CH2:35][C@:33]2([C:38]2[CH:43]=[C:42]([Cl:44])[CH:41]=[C:40](Br)[CH:39]=2)[N:34]=1)C(OC)=O)=O)(C)(C)C>CN(C=O)C.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]>[Cl:44][C:42]1[CH:43]=[C:38]([C@:33]23[CH2:35][CH2:36][CH2:37][C@H:32]2[CH2:31][S:30][C:29]([NH2:24])=[N:34]3)[CH:39]=[C:40]([C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:41]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 67278846HCID 67278846, compound

Product 1

HCID 57827644HCID 57827644, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

2-Fluoropyridine-3-boronic acid (55.8 mg), tetrakis(triphenylphosphine)palladium (0) (22.9 mg) and a 1 N sodium carbonate solution (396 μL) were added to a solution of the by-product (±)-N-(t-butoxycarbonyl)-N-(methoxycarbonyl)[(4aR*,7aS*)-7a-(3-bromo-5-chlorophenyl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl]amine obtained in Preparation Example 71-(2) (100 mg) in DMF (5 mL). After replacement with nitrogen, the mixture was stirred at 85° C. for three hours. The reaction solution was returned to room temperature, and the solvent was evaporated under reduced pressure. The residue was purified by NH-silica gel column chromatography to obtain a crude product. The crude product was further sequentially purified by NH-pTLC and silica gel column chromatography to obtain the title compound (25.6 mg).

Workup

  1. customwas returned to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by NH-silica gel column chromatography
  4. customto obtain a crude product
  5. customThe crude product was further sequentially purified by NH-pTLC and silica gel column chromatography

Sources & evidence

ORD record
ord-7cf387a4c2bc47129fd3c315814f100f
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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