Hydrochloric Acid → HCID 54300597, 화합물

HRID 1683986노트

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HRID 1683986 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([O:16][CH3:17])=[O:15].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Br:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1.Cl>C1COCC1.CN1C(=O)N(C)CCC1>[Br:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:6]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:7]2[CH3:12])=[CH:31][CH:30]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 685274-Bromobenzyl bromideHCID 82067methyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetateHCID 3251421Potassium bis(trimethylsilyl)amide

생성물 1

HCID 54300597HCID 54300597, 화합물수율 48%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-용매

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온도
0 °C

실험 절차

To a solution of ester from Step 1 (13.8 g, 59 mmol) in THF (300 mL) and DMPU (40 mL) at -78° C. was added KHMDS solution (0.64M/toluene, 95 mL, 60 mmol). The reaction mixture was warmed to 0° C. and was then recooled to -78° C., at which point a solution of 4-bromobenzyl bromide (17.0 g, 68 mmol) in THF (80 mL) was added via double-tipped needle. The reaction was allowed to warm to r.t., and was then poured into 1M HCl (500 mL). The product was extracted with Et2O and the organic phase was washed with H2O and brine. After drying (MgSO4), filtration, and removal of solvent, the crude product was purified by flash chromatography (1:20 EtOAc/toluene). The resulting prodeuct was recrystallized from CH2Cl2 /hexane to give 11.4 g of the title compound.

후처리

  1. customwas then recooled to -78° C., at which point
  2. additionwas added via double-tipped needle
  3. temperatureto warm to r.t.
  4. extractionThe product was extracted with Et2O
  5. washthe organic phase was washed with H2O and brine
  6. customAfter drying
  7. filtration(MgSO4), filtration, and removal of solvent
  8. customthe crude product was purified by flash chromatography (1:20 EtOAc/toluene)
  9. customThe resulting prodeuct was recrystallized from CH2Cl2 /hexane

출처 및 근거

ORD 기록
ord-5d03c8c0fcdc4883b2d09df3cd31c2d3
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639780

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