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1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → Carbamic acid, N-[1-(6-hydroxy-3-quinolinyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl ester

HRID 2175136
ノート
印刷プレビュー

反応式

HRID 2175136 の反応式
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9](Br)=[CH:8]2)(=O)C.[NH:16]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17]1.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.CC([O-])(C)C.[K+]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9]([N:16]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:17]1)=[CH:8]2
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

7

反応物 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 23665647Potassium tert-butoxideHCID 685300473-Bromoquinolin-6-yl acetate

生成物 1

HCID 86696256Carbamic acid, N-[1-(6-hydroxy-3-quinolinyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl ester収率 12%

試薬・触媒・溶媒

2
HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

A mixture of Intermediate A (1.50 g, 5.07 mmol), tert-butyl pyrrolidin-3-ylcarbamate (1.13 g, 6.09 mmol), Pd2(dba)3 (0.232 g, 0.254 mmol), Xantphos (0.294 g, 0.507 mmol) and KOtBu (1.14 g, 10.2 mmol) in DMF (15 mL) was bubbled with argon for 20 min. The result mixture was heated at 110° C. overnight. The solution was cooled to rt and the solvent was removed under reduced pressure. The residue was diluted with water, extracted with DCM three times. The combined organic phase was dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by chromatography (eluting with 5% MeOH in DCM) to give the title compound as yellow solid (0.2 g, yield 11%). LCMS (method N): [M+H]+=330, tR=1.93 min.

後処理

  1. customwas bubbled with argon for 20 min
  2. temperatureThe solution was cooled to rt
  3. customthe solvent was removed under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with DCM three times
  6. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by chromatography (eluting with 5% MeOH in DCM)

出典と根拠

ORDレコード
ord-dc9dd3fcf64d4589bb1e0468547c6b64
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09062045B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート