Potassium Carbonate → {(1S,4S)-4-[2-(2-Methoxy-acetylamino)-pyridin-4-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-carbamic acid tert-butyl ester

HRID 1402101ノート

反応式

HRID 1402101 の反応式
[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](Cl)[CH:20]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:27][O:28][CH2:29][C:30]([NH2:32])=[O:31].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:32][C:30](=[O:31])[CH2:29][O:28][CH3:27])[CH:20]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 1400602-MethoxyacetamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86686964[(1S,4S)-4-(2-Chloro-pyridin-4-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-carbamic acid tert-butyl ester

生成物 1

HCID 86686965{(1S,4S)-4-[2-(2-Methoxy-acetylamino)-pyridin-4-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-carbamic acid tert-butyl ester収率 44%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

Intermediate 10b (562 mg, 1.50 mmol), 2-methoxyacetamide (334 mg, 3.75 mmol), Xantphos (173 mg, 0.30 mmol) and potassium carbonate (518 mg, 3.75 mmol) were suspended in 1,4-dioxane (20 mL), warmed, degassed, and placed under argon. To this mixture palladium acetate (34.0 mg, 0.15 mmol) was added. The mixture was degassed and then heated at reflux for 17 h. After cooling, the mixture was filtered through Celite, washing with DCM, and evaporated to a yellow gum. Purification by FCC, eluting with 0-100% ethyl acetate in cyclohexane, gave the title compound as a white foam (281 mg, 44%). LCMS (Method 3): Rt 3.27 min, m/z 450.2 [MNa+].

後処理

  1. temperaturewarmed
  2. customdegassed
  3. customThe mixture was degassed
  4. temperatureheated
  5. temperatureat reflux for 17 h
  6. temperatureAfter cooling
  7. filtrationthe mixture was filtered through Celite
  8. washwashing with DCM
  9. customevaporated to a yellow gum
  10. customPurification by FCC
  11. washeluting with 0-100% ethyl acetate in cyclohexane

出典と根拠

ORDレコード
ord-ea31c8d79ffb4cbbae4895b6d4bc4a7f
出典データセット
uspto-grants-2014_12
特許番号
US08907094B2

反応ノート

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