Ethyl Acetate → HCID 53241673, compound

HRID 1914909Notes

Reaction equation

HRID 1914909 reaction equation
C[Si](C)(C)[O-].[K+].[CH:7]1([S:10]([N:13]2[C:17]3[C:18]4[O:22][CH:21]=[CH:20][C:19]=4[C:23]([F:26])=[C:24]([F:25])[C:16]=3[N:15]([C:27]3[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=3[F:34])C2=O)(=[O:12])=[O:11])[CH2:9][CH2:8]1.C(OCC)(=O)C>C1COCC1.CCCCCC.C(Cl)Cl>[F:26][C:23]1[C:19]2[CH:20]=[CH:21][O:22][C:18]=2[C:17]([NH:13][S:10]([CH:7]2[CH2:8][CH2:9]2)(=[O:12])=[O:11])=[C:16]([NH:15][C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])[C:24]=1[F:25]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 23668039Potassium trimethylsilanolateHCID 67261447HCID 67261447, compound

Product 1

HCID 53241673HCID 53241673, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
27.5 °C

Procedure

Potassium trimethyl silanolate (0.019 g, 0.1498 mmol) was added to a solution of 1-(cyclopropylsulfonyl)-4,5-difluoro-3-(2-fluoro-4-iodophenyl)-1H-benzofuro[6,7-d]imidazol-2(3H)-one (0.04 g, 0.0749 mmol) in THF (5 mL) at 0° C. The reaction mass was stirred for 4 hours at 20-35° C. The reaction was monitored by TLC (25% 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 water, brine solution and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (20% ethyl acetate in hexane) afforded 0.025 g of the product (66% yield). 1H NMR (CDCl3, 300 MHz): δ 7.72 (d, 1H), 7.40 (dd, 1H), 7.28 (d, 1H), 6.99 (d, 1H), 6.95 (bs, 1H), 6.38-6.641 (t, bs, 2H), 2.58-2.62 (m, 1H), 1.11-1.19 (m, 2H), 0.83-0.98 (m, 2H). LCMS: 96.54%, m/z=506.7 (M−1). HPLC: 96.31%

Workup

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

Sources & evidence

ORD record
ord-b0bc1ab74e4f4769a06bc46eae588345
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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