Potassium Carbonate → HCID 58213743、化合物

HRID 340201ノート

反応式

HRID 340201 の反応式
C(OC([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O)=O)(C)(C)C.Br[C:19]1[C:20]([C:27]#[N:28])=[N:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CO.ClCCl.O>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]2[C:20](=[C:27]([NH2:28])[N:8]=[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]3=2)[N:21]=1

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 2773226(2-BOC-aminophenyl)boronic acidHCID 534856273-Bromo-6-methoxypyridine-2-carbonitrile

生成物 1

HCID 58213743HCID 58213743、化合物

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A solution of 2-(tert-butoxycarbonylamino)phenylboronic acid (1.0 eq.) and 3-bromo-6-methoxypicolinonitrile (from step 1) (1.0 eq.) in toluene (0.44 M) was mixed with tetrakis(triphenyl-phosphine)palladium (5 mol %) and 2N aqueous potassium carbonate solution (2.0 eq.). The reaction was heated to 100° C. and stirred overnight. After cooling to ambient temperature, the reaction content was diluted with 2% methanol in dichloromethane and water. The two phases were separated, and the aqueous layer was extracted twice with 2% methanol in dichloromethane. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude product was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-50% ethyl acetate in hexane to give 3-methoxybenzo[f][1,7]naphthyridin-5-amine as a yellow solid. 1H NMR (acetone d-6): δ 8.91 (d, 1H), 8.34 (d, 1H), 7.63 (d, 1H), 7.51-7.53 (dd, 1H), 7.27-7.33 (m, 2H), 6.65 (br, 2H), 4.11 (s, 3H). LRMS [M+H]=226.1

後処理

  1. temperatureAfter cooling to ambient temperature
  2. customThe two phases were separated
  3. extractionthe aqueous layer was extracted twice with 2% methanol in dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated en vacuo
  7. customThe crude product was purified by flash chromatography on a COMBIFLASH® system (ISCO)

出典と根拠

ORDレコード
ord-fbb593076b3e458499a850d113c39646
出典データセット
uspto-grants-2014_11
特許番号
US08895577B2

反応ノート

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