Silane, (ethenyloxy)trimethyl- → 2-(4-(7-Chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-ylcarbon-yl)-2-methoxyphenyl)acetaldehyde

HRID 1908182

反応式

HRID 1908182 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:28][CH2:27][C:13]3([C:18]4=[CH:19][CH:20]=[CH:21][N:17]4[C:16]4[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:15]=4[O:14]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[O:29][CH3:30].C[Si](C)(C)[O:33][CH:34]=[CH2:35]>CN(C=O)C.F[Zn]F>[Cl:26][C:24]1[CH:23]=[CH:22][C:16]2[N:17]3[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]3([CH2:27][CH2:28][N:10]([C:8]([C:5]4[CH:6]=[CH:7][C:2]([CH2:35][CH:34]=[O:33])=[C:3]([O:29][CH3:30])[CH:4]=4)=[O:9])[CH2:11][CH2:12]3)[O:14][C:15]=2[CH:25]=1

参加物

5

反応物 2

HCID 80344Silane, (ethenyloxy)trimethyl-HCID 58551353(4-Bromo-3-methoxy-phenyl)-(7'-chlorospiro[piperidine-4,4'-pyrrolo[2,1-c][1,4]benzoxazine]-1-yl)methanone

生成物 1

HCID 585508322-(4-(7-Chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-ylcarbon-yl)-2-methoxyphenyl)acetaldehyde

試薬・触媒・溶媒 2

HCID 24551Zinc fluoride触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a microwave vial was added Pd(tBu3P)2 (128 mg, 0.250 mmol) and difluorozinc (259 mg, 2.50 mmol). The vial was capped and purged with nitrogen for 10 minutes. DMF (1 mL) was added and the mixture was stirred for 10 minutes. A solution of (4-bromo-3-methoxy-phenyl)-(7′-chlorospiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-yl)methanone (244 mg, 0.500 mmol) in DMF (1.5 mL) was added followed by trimethyl(vinyloxy)silane (581 mg, 5.00 mmol). The reaction mixture was heated at 80° C. for 1 h before it was quenched with brine and extracted with EtOAc (3×). The combined organic layers were dried over sodium sulfate and the solvent was removed. The crude reaction was purified by silica gel chromatography (5%-80% ethyl acetate/hexanes) to give 2-(4-(7-chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-ylcarbon-yl)-2-methoxyphenyl)acetaldehyde.

後処理

  1. customThe vial was capped
  2. custompurged with nitrogen for 10 minutes
  3. additionDMF (1 mL) was added
  4. customwas quenched with brine
  5. extractionextracted with EtOAc (3×)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. customthe solvent was removed
  8. customThe crude reaction
  9. customwas purified by silica gel chromatography (5%-80% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-719374c078a843188857df2340e8c9ac
出典データセット
uspto-grants-2013_12
特許番号
US08598164B2

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