Dimethylformamide → HCID 69508855, compound

HRID 1593692Notes

Reaction equation

HRID 1593692 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][CH:9]2[C:14]([CH3:16])([CH3:15])[C@H:13]3[CH2:17][C@:10]2([CH3:18])[CH2:11][CH2:12]3)=[O:7])=[CH:4][C:3]=1[S:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)(=[O:23])=[O:22].[C:30]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:35]=CC=C[CH:31]=1.C(NCC)C.[Cl-].[NH4+].CN(C)[CH:58]=[O:59]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:58][O:59][CH2:31][C:30]#[C:35][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][CH:9]2[C:14]([CH3:16])([CH3:15])[C@H:13]3[CH2:17][C@:10]2([CH3:18])[CH2:11][CH2:12]3)=[O:7])=[CH:4][C:3]=1[S:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)(=[O:23])=[O:22]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 68852883HCID 68852883, compound

Product 1

HCID 69508855HCID 69508855, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
125 °C

Procedure

A solution of 4-bromo-3-(morpholinosulfonyl)-N-((1S,4R)-1,3,3-trimethylbicyclo-[2.2.1]heptan-2-yl)benzamide 91 (400 mg, 0.8 mmol), bis(triphenylphosphine)-palladium(II) chloride (30 mg, 0.04 mmol), triphenylphosphine (39.7 mg, 0.151 mmol), copper(I) iodide (9 mg, 0.04 mmol), N-ethylethanamine (1.18 mL, 11.4 mmol) in N,N-dimethylformamide (1 mL) was degassed with nitrogen and sonicated. The reaction mixture was heated in the microwave at 125° C. for 25 minutes. The reaction mixture was poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by silica gel chromatography using hexane/ethyl acetate (0-50%) to give the product 6.1 as a yellow oil (240 mg, 60% yield).

Workup

  1. customsonicated
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-04ed7dffce244b5383be8a9a6280ae53
Source dataset
uspto-grants-2007_11
Patent number
US07297796B2

Reaction notes

Loading…