Pyridine → HCID 131736060, compound

HRID 1050269Notes

Reaction equation

HRID 1050269 reaction equation
[C:1]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:12]=[C:11]3[N:13]=[C:14]([O:24][C@H:25]4[CH2:30][O:29][C@H:28]([CH2:31][OH:32])[C@@H:27]([O:33][Si:34]([CH2:39][CH3:40])([CH2:37][CH3:38])[CH2:35][CH3:36])[CH2:26]4)[N:15]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:10]3=[CH:9][C:8]=2[Cl:41])=[CH:3][CH:2]=1.N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]1([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:12]=[C:11]3[N:13]=[C:14]([O:24][C@H:25]4[CH2:30][O:29][C@H:28]([CH:31]=[O:32])[C@@H:27]([O:33][Si:34]([CH2:37][CH3:38])([CH2:39][CH3:40])[CH2:35][CH3:36])[CH2:26]4)[N:15]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:10]3=[CH:9][C:8]=2[Cl:41])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 159087TriacetoxyperiodinaneHCID 90043134HCID 90043134, compound

Product 1

HCID 131736060HCID 131736060, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ((2R,3 S,5R)-5-((5-([1,1′-biphenyl]-4-yl)-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)-3-((triethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methanol (56 mg, 0.080 mmol) in anhydrous DCM under nitrogen was added pyridine (13 μL, 12.7 mg, 0.161 mmol) and Dess-Martin periodinane (51 mg, 0.121 mmol). After stirring at room temperature for 2 hours, the mixture was directly loaded onto a Biotage™ 10 g silica gel cartridge and eluted with 0-20% EtOAc in 1:1 Hexane/DCM over 20 column volumes. The desired SEM regioisomeric product fractions were combined and concentrated under reduced pressure to provide the title compound as a clear oil. LC-MS: calculated for C36H48ClN3O5Si2 693.28, observed m/e: 694.25 (M+H)+ (Rt 3.23/4 min, minor isomer), 694.23 (M+H)+ (Rt 3.31/4 min, major isomer).

Workup

  1. washeluted with 0-20% EtOAc in 1:1 Hexane/DCM over 20 column volumes
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d29a9f44a5d246c09b34f2a958f3fb56
Source dataset
uspto-grants-2016_07
Patent number
US09382243B2

Reaction notes

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