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2-Methyl-2-butene → 6-fluoro-5-[4-(1-hydroxycyclobutyl)-3-methoxyphenyl]-1H-indole-3-carboxylic acid

HRID 338290
ノート
印刷プレビュー

反応式

HRID 338290 の反応式
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=O)=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2([OH:23])[CH2:22]O[CH2:20]2)=[C:15]([O:24][CH3:25])[CH:14]=1.[CH3:26]C(=CC)C.Cl([O-])=O.[Na+].[OH2:35].[OH2:36].P([O-])(O)(O)=O.[Na+]>CC#N.O.C(O)(C)(C)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:36])=[O:35])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2([OH:23])[CH2:20][CH2:26][CH2:22]2)=[C:15]([O:24][CH3:25])[CH:14]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 866986366-fluoro-5-[4-(3-hydroxyoxetan-3-yl)-3-methoxyphenyl]-1H-indole-3-carbaldehyde

生成物 1

HCID 866986386-fluoro-5-[4-(1-hydroxycyclobutyl)-3-methoxyphenyl]-1H-indole-3-carboxylic acid収率 8.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 6386tert-Butanol溶媒

反応条件

温度
0 °C

実験手順

6-fluoro-5-[4-(3-hydroxyoxetan-3-yl)-3-methoxyphenyl]-1H-indole-3-carbaldehyde (86 mg, 0.2534 mmol) was dissolved in MeCN (6 mL) and warm t-butanol (6 mL). 2-methyl-2-butene (4 mL) was then added and cooled to 0° C. Sodium chlorite (342 mg, 5.07 mmol) and sodium dihydrogen phosphate dihydrate (791 mg, 5.07 mmol) were dissolved in water (3 mL). The aqueous solution was added to the organic solution dropwise via addition funnel and the ice bath was removed and the mixture was allowed to warm to room temperature. The reaction was quenched with saturated aqueous sodium sulfite, concentrated to remove the organics and extracted with EtOAc (20 mL×3). The combined organics were washed with brine (20 mL), dried and concentrated to give a crude residue, which was purified by prep HPLC to afford the title compound (7.3 mg, 8.1%) as an off-white solid.

後処理

  1. additionThe aqueous solution was added to the organic solution dropwise via addition funnel
  2. customthe ice bath was removed
  3. temperatureto warm to room temperature
  4. customThe reaction was quenched with saturated aqueous sodium sulfite
  5. concentrationconcentrated
  6. customto remove the organics and
  7. extractionextracted with EtOAc (20 mL×3)
  8. washThe combined organics were washed with brine (20 mL)
  9. customdried
  10. concentrationconcentrated
  11. customto give a crude residue, which
  12. customwas purified by prep HPLC

出典と根拠

ORDレコード
ord-8e4ee619e53347b19a6b055ddb7436ac
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08889730B2

反応ノート

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