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Potassium Phosphate, Tribasic → [6-Fluoro-3-methyl-4-(4-methyl-benzyl)-naphthalen-2-yl]-acetic acid methyl ester

HRID 1644749
ノート
印刷プレビュー

反応式

HRID 1644749 の反応式
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13](OS(C(F)(F)F)(=O)=O)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:24])[CH:11]=2)[CH:6]=1.CC1(C)C(C)(C)OB([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=2)O1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:24])[CH:11]=2)[CH:6]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 162181494,4,5,5-Tetramethyl-2-(4-methylbenzyl)-1,3,2-dioxaborolaneHCID 59326772(6-Fluoro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester

生成物 1

HCID 59350825[6-Fluoro-3-methyl-4-(4-methyl-benzyl)-naphthalen-2-yl]-acetic acid methyl ester
収率 74.9%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

A mixture of (6-fluoro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester (220 mg, 0.578 mmol), 4,4,5,5-tetramethyl-2-(4-methyl-benzyl)-1,3,2-dioxaborolane (402 mg, 1.731 mmol), palladium(II) acetate (17 mg, 0.0757 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (53 mg, 0.129 mmol), potassium phosphate (246 mg, 1.159 mmol), toluene (5 mL) and water (0.5 mL) was heated at 110° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and washed with brine (25 mL). The organic phase was dried over MgSO4, filtered and concentrated. Silica gel chromatography (93:7 hexanes-ethyl acetate) gave 145.7 mg (74.9%) of [6-fluoro-3-methyl-4-(4-methyl-benzyl)-naphthalen-2-yl]-acetic acid methyl ester as a colorless oil which solidified on standing. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.92 (dd, J=8.8, 6.2 Hz, 1 H), 7.75 (s, 1 H), 7.63 (dd, J=12.4, 2.1 Hz, 1 H), 7.33 (td, J=8.8, 2.1 Hz, 1 H), 7.03 (d, J=7.8 Hz, 2 H), 6.92 (d, J=7.8 Hz, 2 H), 4.40 (s, 2 H), 3.93 (s, 2 H), 3.64 (s, 3 H), 2.30 (s, 3 H), 2.21 (s, 3 H).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with brine (25 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-47c9c7c664c8490496879a551bf61e7c
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08124629B2

反応ノート

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