Sodium Carbonate → [3-Chloro-5-[2-[1-[5-(3-fluorophenyl)thiazole-2-yl]-4-pyrrolidine-1-ylpiperidine-4-yl]ethoxy]phenyl]acetic acid

HRID 420602Notes

Reaction equation

HRID 420602 reaction equation
Br[C:2]1[S:6][C:5]([N:7]2[CH2:12][CH2:11][C:10]([CH2:18][CH2:19][O:20][C:21]3[CH:22]=[C:23]([CH2:28][C:29]([OH:31])=[O:30])[CH:24]=[C:25]([Cl:27])[CH:26]=3)([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:9][CH2:8]2)=[N:4][CH:3]=1.[F:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=O>[Cl:27][C:25]1[CH:24]=[C:23]([CH2:28][C:29]([OH:31])=[O:30])[CH:22]=[C:21]([O:20][CH2:19][CH2:18][C:10]2([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:11][CH2:12][N:7]([C:5]3[S:6][C:2]([C:37]4[CH:36]=[CH:35][CH:34]=[C:33]([F:32])[CH:38]=4)=[CH:3][N:4]=3)[CH2:8][CH2:9]2)[CH:26]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 66657808[3-[2-[1-(5-Bromothiazole-2-yl)-4-pyrrolidine-1-ylpiperidine-4-yl]ethoxy]-5-chlorophenyl]acetic acid

Product 1

HCID 57966811[3-Chloro-5-[2-[1-[5-(3-fluorophenyl)thiazole-2-yl]-4-pyrrolidine-1-ylpiperidine-4-yl]ethoxy]phenyl]acetic acidYield 24%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of [3-[2-[1-(5-bromothiazole-2-yl)-4-pyrrolidine-1-ylpiperidine-4-yl]ethoxy]-5-chlorophenyl]acetic acid (60 mg), 3-fluorophenyl boronic acid (32 mg), tetrakis (triphenylphosphine) palladium (13 mg), 1M sodium carbonate (0.55 mL) and dimethylformamide (1 mL) was reacted with a microwave reaction device at 180° C. for 5 minutes. The insoluble material was filtrated. To the filtrate was added formic acid. The solvent was evaporated under reduced pressure and the residue was purified by high performance liquid chromatography to give the title compound (14.4 mg). Yield: 24%.

Workup

  1. customwas reacted with a microwave reaction device at 180° C. for 5 minutes
  2. filtrationThe insoluble material was filtrated
  3. additionTo the filtrate was added formic acid
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by high performance liquid chromatography

Sources & evidence

ORD record
ord-7f115ff0a20f484bb73ec10810e64a06
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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