Triphenylphosphine → [4-(5-Ethanesulfonyl-3-ethyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

HRID 238650

反応式

HRID 238650 の反応式
[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([O:16][C:17]2[C:22](Br)=[CH:21][C:20]([S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])=[CH:19][N:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:29])[CH:11]=2)[CH:6]=1.[CH2:31](B(O)O)[CH3:32].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([O:16][C:17]2[C:22]([CH2:31][CH3:32])=[CH:21][C:20]([S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])=[CH:19][N:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:29])[CH:11]=2)[CH:6]=1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 521157Ethylboronic acidHCID 59326492[4-(3-Bromo-5-ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

生成物 1

HCID 59326586[4-(5-Ethanesulfonyl-3-ethyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester収率 47.6%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A mixture of [4-(3-bromo-5-ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (42 mg, 0.085 mmol), ethylboronic acid (15 mg, 0.20 mmol), bis(triphenylphosphine)dichloropalladium(II) (7.0 mg, 0.01 mmol), potassium phosphate (64 mg, 0.30 mmol), triphenylphosphine (15.2 mg, 0.05 mmol) and toluene (1 mL) was stirred at 100° C. overnight under an argon atmosphere. The resulting mixture was filtered. The filtrate was concentrated in vacuo. The residue was purified by preparative TLC (20% ethyl acetate in petroleum ether) to afford [4-(5-ethanesulfonyl-3-ethyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (18 mg, 47.6%) as a white solid.

後処理

  1. filtrationThe resulting mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by preparative TLC (20% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-cbf8dc933ca44dbaa04705673f6fb29c
出典データセット
uspto-grants-2014_02
特許番号
US08642629B2

関連ノート

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