Ethyl Acetate → HCID 178440517, compound

HRID 1914893Notes

Reaction equation

HRID 1914893 reaction equation
[F:1][C:2]1[C:10]2[N:11]([C:15]3[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=3[F:22])[C:12](=[O:14])[NH:13][C:9]=2[C:8]2[O:7][CH:6]=[CH:5][C:4]=2[C:3]=1[F:23].[CH2:24]([C:27]1([S:30](Cl)(=[O:32])=[O:31])[CH2:29][CH2:28]1)[CH:25]=[CH2:26].C(OCC)(=O)C>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCCCCC>[CH2:24]([C:27]1([S:30]([IH:21][C:18]2[CH:19]=[CH:20][C:15]([N:11]3[C:10]4[C:2]([F:1])=[C:3]([F:23])[C:4]5[CH:5]=[CH:6][O:7][C:8]=5[C:9]=4[NH:13][C:12]3=[O:14])=[C:16]([F:22])[CH:17]=2)(=[O:32])=[O:31])[CH2:29][CH2:28]1)[CH:25]=[CH2:26]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 441819591-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chlorideHCID 672379484,5-Difluoro-3-(2-fluoro-4-iodophenyl)-1H-benzofuro[6,7-d]imidazol-2(3H)-one

Product 1

HCID 178440517HCID 178440517, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
30 °C

Procedure

TEA (02611 g, 2.581 mmol) was added to a solution of 4,5-difluoro-3-(2-fluoro-4-iodophenyl)-1H-benzofuro[6,7-d]imidazol-2(3H)-one (I-32a: 0.37 g, 0.8604 mmol) in dry DCM (20 mL) at 0° C. This was followed by the addition of 1-allyl-cyclopropanesulfonyl chloride (0.229 g, 1.89 mmol) and catalytic amount of DMAP (10 mg). The reaction mass was stirred for 12 hours at 20-40° C. The reaction was monitored by TLC (20% 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 0.228 g of the product (46% yield). 1H NMR (CDCl3, 300 MHz): δ 7.71 (dd, 3H), 7.30 (t, 1H), 7.00 (s, 1H), 5.56-5.57 (m, 1H), 4.90 (t, 2H), 2.70-2.80 (q, 2H), 1.90-2.05 (m, 2H), 1.10-1.19 (m, 2H). LCMS: 98.85%, m/z=574.4 (M+1). HPLC: 97.1%

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-e6fcc732753347eeb9a990357462ed63
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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