2,6-Lutidine → HCID 86671490, compound

HRID 1914895Notes

Reaction equation

HRID 1914895 reaction equation
N1C(C)=CC=CC=1C.[CH2:9]([C:12]1([S:15]([NH:18][C:19]2[C:27]3[O:26][CH:25]=[CH:24][C:23]=3[C:22]([F:28])=[C:21]([F:29])[C:20]=2[NH:30][C:31]2[CH:36]=[CH:35][C:34]([I:37])=[CH:33][C:32]=2[F:38])(=[O:17])=[O:16])[CH2:14][CH2:13]1)[CH:10]=C.C(OCC)(=[O:41])C>O1CCOCC1.O.CCCCCC.C(Cl)Cl.[Os](=O)(=O)(=O)=O>[F:28][C:22]1[C:23]2[CH:24]=[CH:25][O:26][C:27]=2[C:19]([NH:18][S:15]([C:12]2([CH2:9][CH:10]=[O:41])[CH2:13][CH2:14]2)(=[O:16])=[O:17])=[C:20]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([I:37])=[CH:33][C:32]=2[F:38])[C:21]=1[F:29]

Participants

9

Reactant 3

HCID 79372,6-LutidineHCID 8857Ethyl AcetateHCID 67235382HCID 67235382, compound

Product 1

HCID 86671490HCID 86671490, compoundYield 43%

Reagents, catalysts & solvents 5

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
30 °C

Procedure

2,6-Lutidine (0.077 g, 0.7188 mmol) and NaIO4 (0.307 g, 1.4376 mmol) were added to a solution of 1-allyl-N-(4,5-difluoro-6-(2-fluoro-4-iodophenylamino)benzofuran-7-yl)cyclopropane-1-sulfonamide (I-35a: 0.190 g, 0.3594 mmol) in dioxane (10 mL). This was followed by the addition of osmium tetroxide (0.0045 g, 0.0179 mmol) in water (2 mL). The reaction mass was stirred for 12-16 hours at 20-40° C. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mass was diluted with DCM (50 mL) and partitioned between water and DCM. The organic layer was washed with 2N HCl (20 mL), water, brine solution and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (50% ethyl acetate in hexane) afforded 0.086 g of the product (43% yield). LCMS: 74%, m/z=548.9 (M−1).

Workup

  1. custompartitioned between water and DCM
  2. washThe organic layer was washed with 2N HCl (20 mL), water, brine solution
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product
  5. customPurification by column chromatography on silica gel (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1e477c6c46254f838bc0d5bb0da2c77c
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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