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

HRID 420602
ノート
印刷プレビュー

反応式

HRID 420602 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
触媒
HCID 6228Dimethylformamide溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-7f115ff0a20f484bb73ec10810e64a06
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08097610B2

反応ノート

読み込み中…

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