Triphenylphosphine → 4-(2-(3-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)phenoxy)ethyl)morpholine

HRID 1261261ノート

反応式

HRID 1261261 の反応式
CCOC(/N=N/C(OCC)=O)=O.[F:13][C:14]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[CH:33][C:15]=1[O:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[CH:23]=[C:24]([C:26]3[CH:27]=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=3)[S:25][C:18]=12.[O:40]1[CH2:45][CH2:44][N:43]([CH2:46][CH2:47]O)[CH2:42][CH2:41]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[F:13][C:14]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[CH:33][C:15]=1[O:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]2[CH:23]=[C:24]([C:26]3[CH:27]=[C:28]([CH:29]=[CH:30][CH:31]=3)[O:32][CH2:47][CH2:46][N:43]3[CH2:44][CH2:45][O:40][CH2:41][CH2:42]3)[S:25][C:18]=12

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 5462977Diethyl azodicarboxylateHCID 594244533-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)phenol

生成物 1

HCID 594244694-(2-(3-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)phenoxy)ethyl)morpholine収率 66.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Diethylazodicarboxylate (0.6 mL, 3.84 mmol) was added to the solution of 160 (1.05 g, 2.75 mmol), 2-morpholinoethanol (0.5 mL, 3.84 mmol) and triphenylphosphine (1.01 g, 3.84 mmol) in tetrahydrofuran (27 mL). The reaction mixture was stirred until its completion, quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography, eluent MeOH-DCM (2:98) to afford title compound 161 (906 mg, 66% yield) as a light-yellow solid. LRMS (M+1) 496.3 (100%).

後処理

  1. customquenched with saturated aqueous ammonium chloride
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography, eluent MeOH-DCM (2:98)

出典と根拠

ORDレコード
ord-6cb33b9bbe3e44e18eeb2af0e9ba6a28
出典データセット
uspto-grants-2013_06
特許番号
US08470850B2

反応ノート

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