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

HRID 2391708Notes

Reaction equation

HRID 2391708 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].[Si:29]([O:36][CH2:37][C@H:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[Cl:46])O)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].ClC1C=CC=CC=1[C@H](O)C(O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[Si](Cl)(C(C)(C)C)(C)C.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:29]([O:36][CH2:37][C@@H:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[Cl:46])[O:28][C:21]1[CH:20]=[C:19]([N:18]2[C:12]3[CH:11]=[C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[N:15]=[CH:14][C:13]=3[N:16]=[CH:17]2)[S:23][C:22]=1[C:24]([O:26][CH3:27])=[O:25])([C:32]([CH3:34])([CH3:35])[CH3:33])([CH3:31])[CH3:30]

Participants

9

Reactant 7

HCID 11776TriphenylphosphineHCID 28928tert-Butyldimethylsilyl chlorideHCID 97268Di-tert-butyl azodicarboxylateHCID 6922874(S)-2-Chloromandelic acidHCID 21226445Aluminium lithium hydrideHCID 68766707methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-hydroxythiophene-2-carboxylateHCID 68766914(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(2-chlorophenyl)ethanol

Product 1

HCID 68768690methyl 3-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(2-chlorophenyl)ethoxy]-5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner as described for example B31, 0.5 g of methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-hydroxythiophene-2-carboxylate, 0.44 g of (1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(2-chlorophenyl)ethanol (synthesized starting from (S)-(+)-2-chloromandelic acid in a two step sequence including reduction with LiAlH4 and protection of the primary hydroxy group using tert-butyldimethylsilylchloride), 0.63 g of triphenylphosphine (polymer bound, ˜3 mmol/g) and 0.55 g of di-tert-butyl azodicarboxylate in 10 ml anhydrous dichloromethane yield the title compound.

Workup

  1. customsynthesized

Sources & evidence

ORD record
ord-37f557a40b8640c0a23d729ecab85ab4
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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