Triphenylphosphine → HCID 57881268, compound

HRID 1917271Notes

Reaction equation

HRID 1917271 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:9]=[C:8]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:7]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[CH2:19]([C:8]1[N:7]=[C:6]([CH2:5][CH2:4][NH2:1])[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[N:9]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86257326HCID 86257326, compound

Product 1

HCID 57881268HCID 57881268, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step C (0.066 g, 0.2 mmol) in THF (2 mL) was added PPh3 (0.059 g, 2.2 mmol). After 18 h, water was added (0.10 mL) and the mixture was stirred for 48 h. The mixture was diluted with water and extracted with CH2Cl2 (2×). The combined organic layers were dried and concentrated. The resulting residue was purified via SiO2 chromatography (5-15% EtOAc/hexanes) to give 0.060 g (99%) of the title compound. MS (ESI): exact mass calcd. for C20H21N3, 303.17; m/z found, 304.4 [M+H]+. 1H NMR (CDCl3): 7.98-7.96 (m, 2H), 7.45-7.44 (m, 2H), 7.36 (s, 1H), 7.32-7.28 (m, 4H), 7.23-7.19 (m, 1H), 4.31 (s, 2H), 3.13 (t, J=6.5, 2H), 2.91 (t, J=6.5, 2H), 2.42 (s, 3H).

Workup

  1. extractionextracted with CH2Cl2 (2×)
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customThe resulting residue was purified via SiO2 chromatography (5-15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e7cbb177b801419aa4848edcc2b07f58
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Reaction notes

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