1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 2-[(3R,3aR,6R,6aS)-6-[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilyl-ethoxy-methyl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]acetate

HRID 929220Notes

Reaction equation

HRID 929220 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:22]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:21](S(C)(=O)=O)=[N:20][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.[OH:35][C@H:36]1[C@H:40]2[O:41][CH2:42][CH:43]([CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[C@H:39]2[O:38][CH2:37]1.C1CCN2C(=NCCC2)CC1>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[N:22]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:21]([O:35][C@H:36]3[C@H:40]4[O:41][CH2:42][C@@H:43]([CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[C@H:39]4[O:38][CH2:37]3)=[N:20][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 682826082-[[6-Chloro-2-methylsulfonyl-5-(4-phenylphenyl)imidazo[4,5-b]pyridin-1-yl]methoxy]ethyl-trimethyl-silaneHCID 90042054ethyl 2-((3aR,6R,6aR)-6-hydroxyhexahydro-furo[3,2-b]furan-3-yl)acetate

Product 1

HCID 131735097Ethyl 2-[(3R,3aR,6R,6aS)-6-[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilyl-ethoxy-methyl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[[6-chloro-2-methylsulfonyl-5-(4-phenylphenyl)imidazo-[4,5-b]pyridin-1-yl]-methoxy]ethyl-trimethyl-silane (357 mg, 0.694 mmol), ethyl 2-[(3aR,6R,6aR)-6-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]acetate (180 mg, 0.832 mmol), and DBU (150 uL, 0.995 mmol) in DMF (1.0 ml) was stirred at room temperature for 1 hour. The reaction mixture was diluted with EtOAc (200 ml), washed with water (5×30 ml), brine (1×10 mL), dried over MgSO4, filtered, and evaporated under reduced pressure to give the title compound as a mixture of isomers. C34H40ClN3O6Si 649.24 observed m/e: 650.28 (M+H)+ (Rt 1.09 and 1.17/2 min)

Workup

  1. washwashed with water (5×30 ml), brine (1×10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1f31d730d873401db1f8cb6bad2f0cdf
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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