Triphenylphosphine → Methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxylate

HRID 2391691Notes

Reaction equation

HRID 2391691 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]=[CH:17][N:18]([C:19]3[S:23][C:22]([C:24]([O:26][CH3:27])=[O:25])=[C:21]([OH:28])[CH:20]=3)[C:12]=2[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:29][C:30]([F:41])([F:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C@@H:37](O)[CH3:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>ClCCl>[Si:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]=[CH:17][N:18]([C:19]3[S:23][C:22]([C:24]([O:26][CH3:27])=[O:25])=[C:21]([O:28][C@@H:37]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[C:30]([F:29])([F:40])[F:41])[CH3:38])[CH:20]=3)[C:12]=2[CH:11]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 7003730(1S)-1-(2-(trifluoromethyl)phenyl)ethan-1-olHCID 68766707methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-hydroxythiophene-2-carboxylate

Product 1

HCID 68767242Methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, 4.45 g of methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-hydroxythiophene-2-carboxylate and 3.02 g of (1S)-1-[2-(trifluoromethyl)phenyl]ethanol are dissolved in 140 ml anhydrous dichloromethane. 7.07 g triphenylphosphine (polymer bound, ˜3 mmol/g) and 4.88 g of di-tert-butyl azodicarboxylate are added. The reaction mixture is stirred at room temperature for 90 minutes and then filtered. The filter cake is washed with 10 ml dichloromethane and 10 ml methanol. The filtrate is concentrated to dryness under reduced pressure.

Workup

  1. filtrationfiltered
  2. washThe filter cake is washed with 10 ml dichloromethane and 10 ml methanol
  3. concentrationThe filtrate is concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-04fe9134c9aa4a8eb24b56753cc9f399
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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