Triphenylphosphine → HCID 59370710, compound

HRID 1873982Notes

Reaction equation

HRID 1873982 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:3]=1.[CH2:19]([N:26]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:27][CH2:28]O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C(/N=N/C(N(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:28][CH2:27][N:26]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:8][CH:9]=2)[N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 22657Ethanol, 2-[bis(phenylmethyl)amino]-HCID 5353800DiamideHCID 135869969HCID 135869969, compound

Product 1

HCID 59370710HCID 59370710, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl 3-chloro-6-hydroxyindazole-1-carboxylate (4.3611 g) which can be prepared according to the method described in Reference example 39, etc. and 2-(dibenzylamino)ethanol (4.1529 g; manufactured by Tokyo Chemical Industry Co., Ltd.) were dissolved in dehydrated THF (100 mL), added with triphenylphosphine (7.9370 g; manufactured by Kanto Chemical Co., Inc.) and TMAD (5.2270 g; manufactured by Masuda Chemical Industries Co., Ltd.), and then stirred overnight at room temperature. The reaction solution was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in toluene, and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography (“COLUMN-D”; n-hexane:ethyl acetate=90:10→75:25) to obtain the title compound (7.1028 g).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in toluene
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by column chromatography (“COLUMN-D”; n-hexane:ethyl acetate=90:10→75:25)

Sources & evidence

ORD record
ord-749e437dbb7a4095aa73970ed5e73eeb
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

Loading…