Ethyl Acetate → HCID 131735113, compound

HRID 929251Notes

Reaction equation

HRID 929251 reaction equation
C([N:4]1[C:12]2[C:7](=[N:8][C:9](I)=[C:10]([Cl:13])[CH:11]=2)[N:6]=[C:5]1[O:15][C@@H:16]1[CH2:20][O:19][C@@H:18]2[C@H:21]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH2:22][O:23][C@H:17]12)C=C.[CH:32]1([C:35]2[C:40]3[N:41]=[CH:42][S:43][C:39]=3[CH:38]=[CH:37][N:36]=2)[CH2:34][CH2:33]1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C.[Cu]I>[Si:25]([O:24][C@H:21]1[CH:18]2[O:19][CH2:20][C@@H:16]([O:15][C:5]3[NH:4][C:12]4[C:7]([N:6]=3)=[N:8][C:9]([C:42]3[S:43][C:39]5[CH:38]=[CH:37][N:36]=[C:35]([CH:32]6[CH2:33][CH2:34]6)[C:40]=5[N:41]=3)=[C:10]([Cl:13])[CH:11]=4)[CH:17]2[O:23][CH2:22]1)([C:28]([CH3:30])([CH3:29])[CH3:31])([CH3:26])[CH3:27]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 585705244-Cyclopropyl[1,3]thiazolo[4,5-c]pyridineHCID 123197088HCID 123197088, compound2×

Product 1

HCID 131735113HCID 131735113, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Palladium tetrakistriphenylphosphine (200.0 mg, 0.173 mmol) was added to a stirred suspension of [(3R,3aR,6R,6aS)-3-(1-allyl-6-chloro-5-iodo-imidazo[4,5-b]pyridin-2-yl)oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy-tert-butyl-dimethyl-silane (500.0 mg, 0.865 mmol, Intermediate 5), 4-cyclopropylthiazolo[4,5-c]pyridine (183.0 mg, 1.038 mmol), cesium carbonate (1.409 g, 4.33 mmol), and copper (I) iodide (99.0 mg, 0.519 mmol) in degassed DMF (3.2 mL). The reaction mixture placed under nitrogen before being heated to 100° C. for 3 h. The reaction mixture was cooled to room temperature and added to EtOAc (80 ml). The mixture filtered and the solids washed with EtOAc (2×30 mL). The filtrate was evaporated under reduced pressure. Flash chromatography of the resulting residue utilizing a 40 g silica RediSep Rf® Gold column and employing a 0-100% EtOAc/hexane gradient afforded the title compound. LC-MS: calculated for C27H32ClN5O4SSi 585.16 observed m/e: 586.17 (M+H)+ (Rt 1.18/1.8 min)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe mixture filtered
  3. washthe solids washed with EtOAc (2×30 mL)
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4a8932f3c3174ef2bef90f831f6e56d6
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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