Sodium Carbonate → HCID 178463239、化合物

HRID 1469155ノート

反応式

HRID 1469155 の反応式
Br[C:2]1[CH:3]=[C:4]([N:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][CH2:17]2)[CH2:14][CH3:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[OH:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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:26]([O:25][C:23]([NH:22][C@H:19]1[CH2:20][CH2:21][C@H:16]([N:13]([CH2:14][CH3:15])[C:4]2[C:5]([CH3:12])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=[C:2]([C:34]3[CH:35]=[CH:36][C:31]([OH:30])=[CH:32][CH:33]=3)[CH:3]=2)[CH2:17][CH2:18]1)=[O:24])([CH3:28])([CH3:27])[CH3:29]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 178463215HCID 178463215、化合物

生成物 1

HCID 178463239HCID 178463239、化合物収率 87%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate (10 g, 21.3 mmol, see, e.g., WO2012142504 (Attorney Docket No. 41478-507001WO)) and (4-hydroxyphenyl)boronic acid (3.5 g, 25.3 mmol) in a mixture of dioxane (225 mL) and water (75 mL), Na2CO3 (8.01 g, 75.5 mmol) was added and the solution was purged with argon for 30 min. Then Pd(PPh3)4 (2.4 g, 2.07 mmol) was added and argon was purged again for another 15 min. Reaction mass was heated at 100° C. for 4 h. On completion, reaction mixture was diluted with water and extracted with ethyl acetate. Combined organic layer was dried over sodium sulfate. Removal of the solvent under reduced pressure followed by column chromatographic purification afforded the title compound (8.9 g, 87% yield).

後処理

  1. additionwas added
  2. customthe solution was purged with argon for 30 min
  3. customargon was purged again for another 15 min
  4. customReaction mass
  5. customOn completion, reaction mixture
  6. extractionextracted with ethyl acetate
  7. dry with materialCombined organic layer was dried over sodium sulfate
  8. customRemoval of the solvent under reduced pressure
  9. customfollowed by column chromatographic purification

出典と根拠

ORDレコード
ord-5bbcb258a24546979a461c790cc25c02
出典データセット
uspto-grants-2015_04
特許番号
US09006242B2

反応ノート

読み込み中…