Potassium Carbonate → HCID 67270604, compound

HRID 601711Notes

Reaction equation

HRID 601711 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[C:34]([F:36])[CH:35]=1)[CH2:5][C@H:6]1[C@@H:10]([C@H:11]2[CH2:20][C:19]3[C:14](=[C:15]([O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:16]=[CH:17][CH:18]=3)[CH2:13][NH:12]2)[O:9][C:8](=[O:32])[NH:7]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:44]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(#N)C>[F:36][C:34]1[CH:33]=[C:4]([CH:3]=[C:2]([F:1])[CH:35]=1)[CH2:5][C@H:6]1[C@@H:10]([C@H:11]2[CH2:20][C:19]3[C:14](=[C:15]([O:21][Si:22]([CH:29]([CH3:30])[CH3:31])([CH:23]([CH3:24])[CH3:25])[CH:26]([CH3:27])[CH3:28])[CH:16]=[CH:17][CH:18]=3)[CH2:13][N:12]2[CH:44]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[O:9][C:8](=[O:32])[NH:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 67271991HCID 67271991, compound

Product 1

HCID 67270604HCID 67270604, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (4S,5R)-4-(3,5-difluorobenzyl)-5-((R)-8-(triisopropylsilyloxy)-1,2,3,4-tetrahydroisoquinolin-3-yl)oxazolidin-2-one Step F (12), 120 mg, 0.23 mmol) in acetonitrile (2 mL) were added potassium carbonate (64 mg, 0.46 mmol) and bromodiphenylmethane (91 mg, 0.37 mmol). This mixture was put on microwave at 75° C. for 2 h and 15 min. Solvent was removed and the crude mixture was purified by silica gel Flash Chromatography to give 120 mg of the title compound (75% yield): 1H NMR (CDCl3, 500 MHz) δ 0.90 (18H, m), 1.06 (3H, m), 2.47 (1H, m), 2.76 (1H, d, J=20 Hz), 3.16-3.23 (2H, m), 3.69 (1H, d, J=20 Hz), 3.75 (1H, m), 4.02 (1H, m), 4.18 (1H, d, J=20 Hz), 4.72 (1H, m), 4.80 (1H, s), 4.92 (1H, s), 6.61 (1H, d, J=10 Hz), 6.76-6.80 (4H, m), 7.03-7.06 (1H, m), 7.17-7.30 (6H, m), 7.39 (4H, t, J=5 Hz). MS (ESI) (M+H)+ 683.31.

Workup

  1. customSolvent was removed
  2. customthe crude mixture was purified by silica gel Flash Chromatography

Sources & evidence

ORD record
ord-df60bb10da4b4585afb65a03a892465a
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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