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 1908182노트

반응식

HRID 1908182 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 24551Zinc fluoride촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-719374c078a843188857df2340e8c9ac
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598164B2

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