Ethyl chloroformate → (+/-)-tert-Butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-2-ethoxy-2-oxoethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174105ノート

反応式

HRID 2174105 の反応式
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH2:11][C:12]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH3:23])=[C:17]4[C:13]=3[CH:14]=[CH:15][N:16]4[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:8][C:7]=2[CH:31]=1)#[N:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl[C:43]([O:45][CH2:46][CH3:47])=[O:44]>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([C:12]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH3:23])=[C:17]4[C:13]=3[CH:14]=[CH:15][N:16]4[C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[C:43]([O:45][CH2:46][CH3:47])=[O:44])=[N:8][C:7]=2[CH:31]=1)#[N:2]

参加物

5

反応物 3

HCID 10928Ethyl chloroformateHCID 2733832Lithium HexamethyldisilazideHCID 86701743tert-Butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

生成物 1

HCID 86701744(+/-)-tert-Butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-2-ethoxy-2-oxoethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of tert-butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 144-A) (60 mg, 0.144 mmol) in THF (2.1 mL) under nitrogen at −78° C. was added LiHMDS (0.359 ml, 0.359 mmol) in THF. After 10 mins, ethyl chloroformate (0.276 mL, 2.87 mmol) was added and the reaction was warmed to room temperature. After 5 mins the reaction was quenched with sat. aq. NH4Cl, the layers were separated and the aqueous layer extracted with EtOAc. The EtOAc layer was concentrated, purified via FCC with Hep/EtOAc to obtain the title compound. MS (ESI+) m/z 490.0 (M+H).

後処理

  1. customAfter 5 mins the reaction was quenched with sat. aq. NH4Cl
  2. customthe layers were separated
  3. extractionthe aqueous layer extracted with EtOAc
  4. concentrationThe EtOAc layer was concentrated
  5. custompurified via FCC with Hep/EtOAc

出典と根拠

ORDレコード
ord-c9453a66eac6486cb507ab229788f510
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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