Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 67775017, compound

HRID 1037566Notes

Reaction equation

HRID 1037566 reaction equation
[CH:1]1([C:4]2[C:12]([CH:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:14][CH:15]=O)=[CH:11][C:10]3[C:6](=[C:7]([C:28]([NH:30][CH3:31])=[O:29])[N:8]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1.C1(C2C(C(S(C)(=O)=O)CC(O)O)=CC3C(=C(C(NC)=O)N(C4C=CC(C)=CC=4)N=3)C=2)CC1.C1(P(=[CH:83][C:84]([O:86][CH2:87][CH3:88])=[O:85])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH:1]1([C:4]2[C:12]([CH:13]([S:17]([CH3:20])(=[O:18])=[O:19])[CH2:14][CH:15]=[CH:83][C:84]([O:86][CH2:87][CH3:88])=[O:85])=[CH:11][C:10]3[C:6](=[C:7]([C:28](=[O:29])[NH:30][CH3:31])[N:8]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 67774005HCID 67774005, compoundHCID 88415470HCID 88415470, compound

Product 1

HCID 67775017HCID 67775017, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of an approximately 1:1 mixture of racemic 5-cyclopropyl-N-methyl-2-(4-methylphenyl)-6-[1-(methylsulfonyl)-3-oxopropyl]-2H-indazole-3-carboxamide (v) and compound (vi) (16 mg, 0.036 mmol) in DCM (10 mL) under argon was added ethyl (triphenyl-λ5-phosphanylidene)acetate (20 mg, 0.057 mmol), and the reaction was stirred at RT under argon for 1 h. The reaction mixture was evaporated to dryness and purified by flash column chromatography eluting with EtOAc/heptane (50-100%) to give racemic ethyl 5-[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)-2H-indazol-6-yl]-5-(methylsulfonyl)pent-2-enoate (vii) as a mixture of E and Z isomers (≈4:1) as an oil (18 mg, 99%).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by flash column chromatography
  3. washeluting with EtOAc/heptane (50-100%)

Sources & evidence

ORD record
ord-2849ef12935e417fb4f2f693b18956f3
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

Loading…