Hydrochloric Acid → HCID 54300597、化合物

HRID 1683986

反応式

HRID 1683986 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 54300597HCID 54300597、化合物収率 48%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5d03c8c0fcdc4883b2d09df3cd31c2d3
出典データセット
uspto-grants-1997_06
特許番号
US05639780

関連ノート

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