Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium trimethylsilanolate | HCID 23668039 | — |
| Reactant | HCID 68313344 | HCID 68313344 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 67237827 | HCID 67237827 | 92.5% |
Reaction Steps
Potassium trimethyl silanolate (0.105 g, 0.8256 mmol) was added to a solution of 1-(2-(benzyloxymethyl)cyclopropylsulfonyl)-4,5-difluoro-3-(2-fluoro-4-iodophenyl)-1H-benzofuro[6,7-d]imidazol-2(3H)-one (I-37a: 0.180 g, 0.2752 mmol) in THF (5 mL) at 0° C. The reaction mass was stirred for 2 hours at 20-40° C. The reaction was monitored by TLC (30% 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 0.160 g of the crude product which was used in the next step without further purification. 1H NMR (CDCl3, 300 MHz): δ 7.52 (d, 1H), 7.40 (d, 1H), 7.32 (t, 1H), 7.20-7.26 (m, 5H), 7.20 (bs, 1H), 6.92 (d, 1H), 632-6.39 (m, 2H), 4.48 (s, 2H), 3.25 (q, 2H), 2.52 (q, 1H), 1.52-1.53 (m, 1H), 1.20-1.23 (m, 1H), 0.90-1.01 (m, 1H). LCMS: 93.86%, m/z=627.9 (M-1). HPLC: 95.59%
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08614239B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-adcd7d7e1cd64da3924939efcd88dbc1 |
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| Source note | uspto-grants-2013_12 |
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