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Cesium carbonate → HCID 86729626、化合物

HRID 2284900
ノート
印刷プレビュー

反応式

HRID 2284900 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16](=[O:19])[CH:17]=[CH2:18])[C:5]([Cl:20])=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]([CH2:32][CH3:33])[C:29](=[O:31])[CH3:30])=[CH:24][C:23]=1[C:34]([F:37])([F:36])[F:35].C(=O)([O-])[O-].[Cs+].[Cs+].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>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:20][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16](=[O:19])[CH:17]=[CH2:18])=[N:7][C:2]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH2:32][CH3:33])[C:29](=[O:31])[CH3:30])=[CH:24][C:23]=2[C:34]([F:35])([F:36])[F:37])=[N:3][CH:4]=1
参加物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 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86729624HCID 86729624、化合物HCID 86729627HCID 86729627、化合物

生成物 1

HCID 86729626HCID 86729626、化合物

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of Intermediate 1 from Example 162 (100 mg, 0.3246 mmol) in tetrahydrofuran (5 mL), N-(4-amino-3-(trifluoro methyl)phenyl)-N-ethylacetamide (80 mg, 0.3246 mmol) and cesium carbonate (316 mg, 0.9738 mmol) were added and degassed for 10 min. To the reaction mixture palladium acetate (38 mg, 0.1623 mmol) and xanthphos (36.8 mg, 0.0973 mmol) were added and again degassed for another 5 min. The mixture was irradiated by microwave at 80° C. for 20 min. TLC showed completion of starting material (TLC system: 10% methanol/chloroform, (Rf): 0.5). The reaction was quenched with water (15 mL) and extracted with ethyl acetate (3×10 mL). The organic layer was separated, dried over sodium sulfate and concentrated. The crude compound was purified by prep-HPLC to obtain the title compound as yellow solid. (30 mg, 17%). 1HNMR (DMSO-d6) δ 0.98 (m, 3H), 1.70 (m, 3H), 1.85 (s, 1H), 3.63 (m, 2H), 5.77-5.80 (dd, 1H J=1.8 Hz and 10.2 Hz), 6.26-6.31 (dd, 1H J=1.8, 17 Hz), 6.44-6.51 (dd, 1H J=10.2, 17 Hz), 7.09-7.17 (m, 2H), 7.32-7.35 (dd, 1H J=1.7, 7.5 Hz), 7.48 (d, 1H J=7.1 Hz), 7.55 (s, 1H), 7.63 (d, 1H J=8.2 Hz), 7.72 (d, 1H J=8.2 Hz), 8.08 (s, 1H), 8.49 (s, 1H), 10.12 (s, 1H). MS m/z: 519.5 (ES+, M+H).

後処理

  1. customdegassed for 10 min
  2. customagain degassed for another 5 min
  3. customThe mixture was irradiated by microwave at 80° C. for 20 min
  4. customThe reaction was quenched with water (15 mL)
  5. extractionextracted with ethyl acetate (3×10 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe crude compound was purified by prep-HPLC

出典と根拠

ORDレコード
ord-bb3a3ae8bd1d44fba017e9651192124f
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09145387B2

反応ノート

読み込み中…

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