1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 89761791, 화합물

HRID 528622노트

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HRID 528622 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH2:10][O:11][CH3:12].[CH3:13][O:14][C:15]1[CH:40]=[CH:39][C:18]([CH2:19][N:20]([C:34]2[S:35][CH:36]=[CH:37][N:38]=2)[S:21]([C:24]2[CH:25]=[CH:26][C:27]3[NH:32][CH2:31][CH2:30][O:29][C:28]=3[CH:33]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=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(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][N:20]([C:34]2[S:35][CH:36]=[CH:37][N:38]=2)[S:21]([C:24]2[CH:25]=[CH:26][C:27]3[N:32]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=4[O:8][CH2:9][CH2:10][O:11][CH3:12])[CH2:31][CH2:30][O:29][C:28]=3[CH:33]=2)(=[O:23])=[O:22])=[CH:39][CH:40]=1

참가 물질

7

반응물 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 137209681-Bromo-2-(2-methoxyethoxy)benzeneHCID 23676156Sodium t-butoxideHCID 89761436N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

생성물 1

HCID 89761791HCID 89761791, 화합물수율 44.4%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

A mixture of 1-bromo-2-(2-methoxyethoxyl)benzene (302.0 mg, 1.31 mmol), INTERMEDIate M (500 mg, 1.19 mmol), Pd2(dba)3 (76.0 mg, 0.0837 mmol), Xantphos (69.0 mg, 0.119 mmol) and sodium-tert-butoxide (229.0 mg, 2.39 mmol) in toluene (10 mL) was degassed with nitrogen for 10 minutes. The reaction mixture was subjected for heating at 100° C. for 1 h under microwave. After completion, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3×15 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by combiflash column chromatography (column size: 12 g; elution: 12% ethyl acetate in hexane) to get N-(4-methoxybenzyl)-4-(2-(2-methoxyethoxyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (300 mg, 44.2%) as yellow solid. MS (ESI, positive ion) m/z: 568.03 (M+1).

후처리

  1. customwas degassed with nitrogen for 10 minutes
  2. additionAfter completion, the reaction mixture was diluted with water (10 mL)
  3. extractionextracted with ethyl acetate (3×15 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain the crude material which
  7. customwas purified by combiflash column chromatography (column size: 12 g; elution: 12% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-651770def0d14f7a9e004fab761c2430
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346798B2

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