Triethylamine → 2-[2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione

HRID 1370407ノート

反応式

HRID 1370407 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[CH:2]1.CCN(CC)CC.C(OCl)(C)(C)C.[CH3:36][C:37]([CH3:49])=[CH:38][CH2:39]B1C2CCCC1CCC2>C1COCC1>[CH3:36][C:37]([C:2]1[NH:1][C:9]2[C:4]([C:3]=1[CH2:10][CH2:11][N:12]1[C:13](=[O:22])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]1=[O:21])=[CH:5][CH:6]=[CH:7][CH:8]=2)([CH3:49])[CH:38]=[CH2:39]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2885772-[2-(1H-indol-3-yl)ethyl]-1H-Isoindole-1,3(2H)-dioneHCID 521297Tert-Butyl hypochloriteHCID 53261919-(3-Methyl-2-butenyl)-9-bora-bicyclo[3.3.1]nonane

生成物 1

HCID 223969612-[2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]ethyl]-1H-isoindole-1,3(2H)-dione

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 2-[2-(1H-indol-3-yl)ethyl]-1H-isoindole-1,3(2H)-dione (3.77 g, 13.0 mmol) in dry THF (0.13 L) under argon was added NEt3 (1.84 mL, 13.0 mmol). This mixture was cooled to −78° C., and neat t-BuOCl (1.54 mL, 13.0 mmol) was added. The reaction mixture was stirred for 30 min at −78° C. A solution of 9-(3-methyl-2-butenyl)-9-bora-bicyclo[3.3.1]nonane (40 mmol) in hexanes was added. The reaction mixture was stirred for 6 h at −78° C. It was quenched with 1 M aq HCl, and permitted to warm to rt overnight. The reaction mixture was extracted with CH2Cl2. The CH2Cl2 extracts were dried, filtered, and concentrated to give an oil. The oil was purified by silica chromatography to give the title compound: TLC Rf=0.36 (CH2Cl2); MS (ESI+) m/z 381.2, 359.2; 1H NMR (300 MHz, CDCl3) δ 7.91 (1H), 7.88-7.69 (5H), 7.29 (1H), 7.10 (2H), 6.18 (1H), 5.25 (2H), 3.95 (2H), 3.16 (2H), 1.61 (6H).

後処理

  1. stirringThe reaction mixture was stirred for 6 h at −78° C
  2. customIt was quenched with 1 M aq HCl
  3. temperatureto warm to rt overnight
  4. extractionThe reaction mixture was extracted with CH2Cl2
  5. dry with materialThe CH2Cl2 extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oil
  9. customThe oil was purified by silica chromatography

出典と根拠

ORDレコード
ord-f3bbe00a5eee4cecb5e94a076f484235
出典データセット
uspto-grants-2003_06
特許番号
US06583135B2

反応ノート

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