Potassium Carbonate → 6-Methyl-4-(2-Phenoxyphenyl)-1,6-Dihydro-7h-Pyrrolo[2,3-C]pyridin-7-One

HRID 930837

反応式

HRID 930837 の反応式
Br[C:2]1[C:3]2[CH:12]=[CH:11][N:10](S(C3C=CC(C)=CC=3)(=O)=O)[C:4]=2[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[O:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[F-].[Cs+].C(=O)([O-])[O-].[K+].[K+]>COCCOC.CO.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.O>[CH3:8][N:6]1[CH:7]=[C:2]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[O:23][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:3]2[CH:12]=[CH:11][NH:10][C:4]=2[C:5]1=[O:9]

参加物

9

反応物 4

HCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 2773559(2-Phenoxyphenyl)boronic acidHCID 896563044-Bromo-1,6-dihydro-6-methyl-1-((4-methylphenyl)sulfonyl)-7H-pyrrolo(2,3-c)pyridin-7-one

生成物 1

HCID 716162976-Methyl-4-(2-Phenoxyphenyl)-1,6-Dihydro-7h-Pyrrolo[2,3-C]pyridin-7-One収率 59.3%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of Example 1e (152 mg, 0.40 mmol), 2-phenoxyphenylboronic acid (0.111 g, 0.520 mmol, 1.3 equivalents), Pd(PPh3)4 (0.023 g, 5 mol %) and cesium fluoride (0.182 g, 1.2 mmol) in DME (3 mL) and methanol (1.5 mL) was heated under microwave condition (120° C., 30 minutes). To this mixture was added potassium carbonate (0.055 g, 0.40 mmol) and water (1 mL) and the reaction mixture was reheated in the microwave oven at 120° C. for another 2 hours. The organic layer was separated and purified by flash chromatography (silica gel, ethyl acetate). The resulting material was triturated with acetone and filtered to provide 0.075 g of the title compound (59%). 1H NMR (500 MHz, DMSO-d6) δ 3.50 (s, 3H), 6.21-6.23 (m, 1H), 6.88 (d, J=7.62 Hz, 2H), 6.99-7.04 (m, 2H), 7.24-7.30 (m, 5H), 7.36-7.40 (m, 1H), 7.50 (dd, J=7.48, 1.68 Hz, 1H), 11.98 (s, 1H). MS (ESI+) m/z 317 (M+H)+.

後処理

  1. customThe organic layer was separated
  2. custompurified by flash chromatography (silica gel, ethyl acetate)
  3. customThe resulting material was triturated with acetone
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-0d2d26b98e6c4c24a774ca8c95f79e98
出典データセット
uspto-grants-2016_03
特許番号
US09296741B2

関連ノート

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