Sodium Carbonate → 5-(4-acetylpyridin-3-yl)-3-methylbenzo[d]oxazol-2(3H)-one

HRID 1253927ノート

反応式

HRID 1253927 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8](=[O:10])[CH3:9].[CH3:11][N:12]1[C:16]2[CH:17]=[C:18](B3OC(C)(C)C(C)(C)O3)[CH:19]=[CH:20][C:15]=2[O:14][C:13]1=[O:30].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:8]([C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:18]1[CH:19]=[CH:20][C:15]2[O:14][C:13](=[O:30])[N:12]([CH3:11])[C:16]=2[CH:17]=1)(=[O:10])[CH3:9]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 137934561-(3-Bromopyridin-4-yl)ethan-1-oneHCID 595350693-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2(3H)-benzoxazolone

生成物 1

HCID 498020215-(4-acetylpyridin-3-yl)-3-methylbenzo[d]oxazol-2(3H)-one収率 55.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

A mixture of 1-(3-bromopyridin-4-yl)ethanone (50 mg, 0.250 mmol), 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2(3H)-one (68.8 mg, 0.250 mmol), polymer bound PalladiumTetrakis (56.8 mg, 6.25 μmol) and sodium carbonate (250 μl, 0.500 mmol) in toluene (1 mL) and ethanol (1 mL) was heated to 90° C. in microwave for 45 min. After filtration through a pad of Na2SO4, the solvent was removed in vacuum. The residue was purified by flash column (MeOH—CH2Cl2, v/v, 1%-1.5%) and yielded colorless solid (37 mg). ESI-MS m/z: 269.0 [M+1]+, Retention time 1.03 min; 1H NMR (400.3 MHz, CDCl3): δ 2.13 (s, 3H), 344 (s, 3H), 6.95 (d, J=1.48 Hz, 1H), 7.07 (dd, J=8.2, 1.68 Hz, 1H), 7.29 (d, J=8.2 Hz, 1H), 7.37 (d J=5 Hz, 1H), 8.69 (s, 1H), 8.73 (d, J=5 Hz, 1H).

後処理

  1. filtrationAfter filtration through a pad of Na2SO4
  2. customthe solvent was removed in vacuum
  3. customThe residue was purified by flash column (MeOH—CH2Cl2, v/v, 1%-1.5%)

出典と根拠

ORDレコード
ord-c04d8fb8b23f452095a50db93690123c
出典データセット
uspto-grants-2013_06
特許番号
US08455522B2

反応ノート

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