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 2174105노트

반응식

HRID 2174105 반응식
[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]

참가 물질

5

반응물 3

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

생성물 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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c9453a66eac6486cb507ab229788f510
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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