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4-(7-bromo-benzooxazol-2-ylamino)-2,N,N-trimethyl-benzamide → 4-[7-(3-Fluoro-4-morpholin-4-ylmethyl-phenyl)-benzooxazol-2-ylamino]-2,N,N-trimethyl-benzamide

HRID 469820
ノート
印刷プレビュー

反応式

HRID 469820 の反応式
Br[C:2]1[C:10]2[O:9][C:8]([NH:11][C:12]3[CH:22]=[CH:21][C:15]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])=[C:14]([CH3:23])[CH:13]=3)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[F:24][C:25]1[CH:37]=[C:36]([Sn](C)(C)C)[CH:35]=[CH:34][C:26]=1[CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:24][C:25]1[CH:37]=[C:36]([C:2]2[C:10]3[O:9][C:8]([NH:11][C:12]4[CH:22]=[CH:21][C:15]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])=[C:14]([CH3:23])[CH:13]=4)=[N:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:35]=[CH:34][C:26]=1[CH2:27][N:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]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

5

反応物 2

HCID 674578214-(7-bromo-benzooxazol-2-ylamino)-2,N,N-trimethyl-benzamideHCID 674580834-(2-Fluoro-4-trimethylstannanyl-benzyl)-morpholine

生成物 1

HCID 591443124-[7-(3-Fluoro-4-morpholin-4-ylmethyl-phenyl)-benzooxazol-2-ylamino]-2,N,N-trimethyl-benzamide

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒
HCID 8071
1,2-Dimethoxyethane
溶媒

反応条件

温度
150 °C

実験手順

0.1 g (0.267 mmol) 4-(7-bromo-benzooxazol-2-ylamino)-2,N,N-trimethyl-benzamide and 0.17 g (0.305 mmol) 4-(2-fluoro-4-trimethylstannanyl-benzyl)-morpholine are dissolved in 2 ml 1,2-dimethoxy-ethane and a stream of argon is bubbled through the mixture in order to exclude oxygen from the reaction mixture. Tetrakis (triphenylphosphine) palladium (0.020 g, 0.016 mmol) is added and the reaction mixture is stirred at 150° C. for 1 h. After that the reaction mixture is poured on water and extracted 3× with EtOAc. The combined organic layers are washed with water and saturated NaCl solution, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, EtOAc:MeOH=95:5; column chromatography followed by thick-layer chromatography) to afford the title compound. Rt=1.67 min (Waters Symmetry C8, 2.1×50 mm, detection 210-250 nM, 5% to 100% CH3CN in H2O in 2 min+0.05% TFA, flow rate 1.0 ml/min); MS: 375 (M+1)+.

後処理

  1. customa stream of argon is bubbled through the mixture in order
  2. additionAfter that the reaction mixture is poured on water
  3. extractionextracted 3× with EtOAc
  4. washThe combined organic layers are washed with water and saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe residue is purified by chromatography (silicagel, EtOAc:MeOH=95:5; column chromatography followed by thick-layer chromatography)

出典と根拠

ORDレコード
ord-894fdc4cb1594457a4992f6135d91a5b
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08629168B2

反応ノート

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