Potassium Iodide → 2-(4-Bromophenyl)-4-{2-[(3R)-3-(fluoromethyl)pyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazole

HRID 1445851Notes

Reaction equation

HRID 1445851 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:20])=[C:11]([CH2:13][CH2:14]OS(C)(=O)=O)[N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].CC1C=CC(S(O)(=O)=O)=CC=1.[F:40][CH2:41][C@@H:42]1[CH2:46][CH2:45][NH:44][CH2:43]1>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:20])=[C:11]([CH2:13][CH2:14][N:44]3[CH2:45][CH2:46][C@@H:42]([CH2:41][F:40])[CH2:43]3)[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11451238Methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester2×HCID 86614638(3R)-3-(Fluoromethyl)pyrrolidine 4-methylbenzenesulfonate2×

Product 1

HCID 116320322-(4-Bromophenyl)-4-{2-[(3R)-3-(fluoromethyl)pyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazoleYield 93.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepare using the method of Example 102 with 2-[2-(4-bromophenyl)-5-methyl-1,3-oxazol-4-yl]ethyl methanesulfonate (See Intermediate 13) (0.36 g, 0.99 mmole), anhydrous acetonitrile (2 mL), potassium carbonate (0.55 g, 3.98 mmol), potassium iodide (0.016 g, 0.10 mmol) and (3R)-3-(fluoromethyl)pyrrolidine 4-methylbenzenesulfonate (salt) (See Intermediate 57) (0.41 g, 1.49 mmol) to give the title compound as a pale orange oil (0.34 g): MS (m/e) (79Br/81Br): 367, 369(M+1)

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-5c397e2734f94e8ea1dbf38523989a2b
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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