Potassium Carbonate → HCID 72695484、化合物

HRID 1773897ノート

反応式

HRID 1773897 の反応式
I[C:2]1[N:11]=[C:10]2[N:4]([CH2:5][CH2:6][C:7]3[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=3[CH:9]2[O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[C:3]=1[CH3:24].[F:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:25][C:26]1[CH:31]=[C:30]([C:2]2[N:11]=[C:10]3[N:4]([CH2:5][CH2:6][C:7]4[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=4[CH:9]3[O:12][CH:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)[C:3]=2[CH3:24])[CH:29]=[CH:28][CH:27]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 86703973HCID 86703973、化合物

生成物 1

HCID 72695484HCID 72695484、化合物

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
95 °C

実験手順

To a solution of 2-iodo-1-methyl-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 133) (100 mg, 0.23 mmole) in toluene (2 mL) and ethanol (1 mL) in a screw-capped vial are added 3-fluorobenzeneboronic acid (64 mg, 0.46 mmole), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (10 mg) and an 1M aqueous solution of potassium carbonate (0.8 mL). The vial is evacuated and filled with argon. The reaction mixture is stirred at 95° C. for 20 hours. Water is added to the reaction mixture, and the pH is adjusted to 9-10 with 1N aqueous sodium hydroxide. The aqueous phase is extracted three times with ethyl acetate. The pooled organic extracts are dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (CH2Cl2:MeOH:NH4OH) as eluent with a gradient from (95:5:0.1) to (92:8:0.5) to give 2-(3-fluorophenyl)-1-methyl-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene melting at 132° C.

後処理

  1. customThe vial is evacuated
  2. additionfilled with argon
  3. additionWater is added to the reaction mixture
  4. extractionThe aqueous phase is extracted three times with ethyl acetate
  5. dry with materialThe pooled organic extracts are dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent is removed under reduced pressure
  8. customThe residue is purified by silica gel chromatography

出典と根拠

ORDレコード
ord-6dcd4acc17c54c12a0e5c212727fb019
出典データセット
uspto-grants-2016_02
特許番号
US09255101B2

反応ノート

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