Triphenylphosphine → HCID 69459764, compound

HRID 1297123Notes

Reaction equation

HRID 1297123 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[N:12]([CH2:23][CH3:24])[C:11](=[O:25])[CH2:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:26]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:27]#[CH:28].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cu]I.Cl[Pd]Cl.CC#N>[CH2:30]([O:29][CH2:26][C:27]#[C:28][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[N:12]([CH2:23][CH3:24])[C:11](=[O:25])[CH2:10][N:9]=2)=[CH:4][CH:3]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 6917484((Prop-2-yn-1-yloxy)methyl)benzeneHCID 10272494HCID 10272494, compound

Product 1

HCID 69459764HCID 69459764, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Stir for 12 hours under an inert atmosphere at 50° C., a mixture of 100 mg (0.27 mmol) of 5-(4-bromophenyl)-1-ethyl-7,8-dimethoxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one (IIbl), 194 mg (1.3 mmol) of [(prop-2-ynyloxy)methyl]benzene, 9.0 mg of CuI, 5.2 mg of PdCl2, 18.0 mg of PPh3, 0.5 ml of TEA, 2 ml of CH3CN. Evaporate to dryness and purify by silica chromatography (AcOEt 1/hexane 1). Recrystallize in EtO2/pentane. Yield: 37%. M: 64–66° C. 1H-NMR (CDCl3, 300 MHz): d 1.12 (s, 3H, CH3), 3.72–3.83 (m, 4H, 1H CH2+OCH3), 4.00 (AB system, ? d=0.63, JAB=13.5, 2H, —NCH2), 4.03 (s, 3H, OCH3), 4.43 (s, 2H, OCH2), 4.69 (m, 2H, ═C—CH2), 4.77 (m, 1H, OCH2), 6.65 (s, 1H Ar), 6.86 (s, 1H Ar), 7.27–7.63 (m, 9H Ar).

Workup

  1. customEvaporate to dryness
  2. custompurify by silica chromatography (AcOEt 1/hexane 1)
  3. customRecrystallize in EtO2/pentane
  4. custom64–66° C

Sources & evidence

ORD record
ord-70982a547d1b48459d73014f86eff30a
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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