Cerium(III) chloride → HCID 178459058、化合物

HRID 76270

反応式

HRID 76270 の反応式
[Cl-].[Ce+3].[Cl-].[Cl-].[C:5]([N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17](=[O:19])[CH3:18])/[C:11](=[N:20]/[C:21](=[O:33])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[C:23]=2[F:32])/[S:10]1)([CH3:8])([CH3:7])[CH3:6].[CH3:34][Mg]Br>C1COCC1>[C:5]([N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])([CH3:34])[CH3:18])/[C:11](=[N:20]/[C:21](=[O:33])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:31])[F:30])[C:23]=2[F:32])/[S:10]1)([CH3:6])([CH3:7])[CH3:8]

参加物

5

反応物 3

HCID 24636Cerium(III) chlorideHCID 178418573HCID 178418573、化合物HCID 178467761HCID 178467761、化合物

生成物 1

HCID 178459058HCID 178459058、化合物収率 55.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To the suspension of cerium(III) chloride (86 mg, 0.35 mmol) in THF (3 mL) was added the product from Example 77 (100 mg, 0.23 mmol) in THF (0.5 mL). The mixture was stirred at rt for 1 hr. The above mixture was cooled to −40° C. and methylmagnesium bromide (41.6 mg, 0.348 mmol) was added dropwise. The reaction was stirred for 40 min at −40° C., quenched with saturated aqueous NH4Cl and extracted with CH2Cl2 (2×). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 57 mg (55%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.23 (s, 6 H) 1.57-1.61 (m, 2 H) 1.68 (s, 9 H) 1.74 (s, 1 H) 1.81-1.89 (m, 2 H) 2.88 (t, J=7.63 Hz, 2 H) 7.30 (t, J=7.93 Hz, 1 H) 7.69 (t, J=6.41 Hz, 1 H) 8.01-8.04 (m, 1 H) 8.39 (td, J=7.93, 1.53 Hz, 1 H); MS (DCI/NH4+) m/z 447 (M+H)+.

後処理

  1. temperatureThe above mixture was cooled to −40° C.
  2. stirringThe reaction was stirred for 40 min at −40° C.
  3. customquenched with saturated aqueous NH4Cl
  4. extractionextracted with CH2Cl2 (2×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-cd573958a6994c6b84dedfa0b816280c
出典データセット
uspto-grants-2014_09
特許番号
US08835475B2

関連ノート

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