Triethylamine → HCID 45121508, compound

HRID 748656Notes

Reaction equation

HRID 748656 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([C:14]2[N:15]=[CH:16][N:17]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:18]=2)(O)[CH3:12])=[CH:3][CH:2]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[C:19]([N:17]1[CH:18]=[C:14]([C:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[CH:2][CH:3]=2)=[CH2:12])[N:15]=[CH:16]1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59751464HCID 59751464, compound

Product 1

HCID 45121508HCID 45121508, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Quinolin-4-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate G3) (4.78 g, 9.93 mmol) in dichloromethane (100 mL) was treated with triethylamine (11.0 mL, 78.9 mmol) at 0° C. Methanesulfonyl chloride (MsCL) (2.3 mL, 29.7 mmol) was added via syringe and the mixture was stirred for 2 h. (see procedure found in Toshima, K et al J Amer. Chem. Soc. 1995 117, 10825; incorporated herein by reference). The mixture was subjected to a typical aqueous work-up. The crude material was purified by chromatography on silica gel with 2% NH3-MeOH: dichloromethane to give 4-[1-(1-trityl-1H-imidazol-4-yl)-vinyl]-quinoline (Intermediate G4) as a tan solid, 3.51 g (76%).

Workup

  1. customThe crude material was purified by chromatography on silica gel with 2% NH3-MeOH

Sources & evidence

ORD record
ord-8f36f2344aa14093bf482ccd15ad854c
Source dataset
uspto-grants-2008_07
Patent number
US07399868B2

Reaction notes

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