Ethyl Acetate → HCID 67237827, compound

HRID 1914897Notes

Reaction equation

HRID 1914897 reaction equation
C[Si](C)(C)[O-].[K+].[CH2:7]([O:14][CH2:15][CH:16]1[CH2:18][CH:17]1[S:19]([N:22]1[C:26]2[C:27]3[O:31][CH:30]=[CH:29][C:28]=3[C:32]([F:35])=[C:33]([F:34])[C:25]=2[N:24]([C:36]2[CH:41]=[CH:40][C:39]([I:42])=[CH:38][C:37]=2[F:43])C1=O)(=[O:21])=[O:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OCC)(=O)C>C1COCC1.CCCCCC.C(Cl)Cl>[CH2:7]([O:14][CH2:15][CH:16]1[CH2:18][CH:17]1[S:19]([NH:22][C:26]1[C:27]2[O:31][CH:30]=[CH:29][C:28]=2[C:32]([F:35])=[C:33]([F:34])[C:25]=1[NH:24][C:36]1[CH:41]=[CH:40][C:39]([I:42])=[CH:38][C:37]=1[F:43])(=[O:20])=[O:21])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 23668039Potassium trimethylsilanolateHCID 68313344HCID 68313344, compound

Product 1

HCID 67237827HCID 67237827, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
30 °C

Procedure

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%

Workup

  1. custompartitioned between water and DCM
  2. washThe organic layer was washed with water, brine solution
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-adcd7d7e1cd64da3924939efcd88dbc1
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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