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Tributylphosphine → Ethyl 7-(2-{[di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate

HRID 1188888
Notes
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Reaction equation

HRID 1188888 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[C:27]([Si:31]([C:43]([CH3:46])([CH3:45])[CH3:44])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[O:32][CH2:33][CH:34](O)[CH3:35])([CH3:30])([CH3:29])[CH3:28].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>O1CCCC1>[C:43]([Si:31]([C:27]([CH3:28])([CH3:30])[CH3:29])([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[O:32][CH2:33][CH:34]([CH3:35])[O:1][C:2]1[CH:3]=[C:4]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2)([CH3:44])([CH3:45])[CH3:46]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 66726144Ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylateHCID 668862121-{[Di-tert-butyl(phenyl)silyl]oxy}propan-2-ol

Product 1

HCID 67118494Ethyl 7-(2-{[di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate
Yield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (2.3 g), 1-{[di-tert-butyl(phenyl)silyl]oxy}propan-2-ol (3.9 g), 1,1′-(azodicarbonyl)dipiperidine (3.1 g), tributylphosphine (3.1 mL) and tetrahydrofuran (20 mL) was stirred at 50° C. for 18 hr. The reaction solution was allowed to cool to room temperature, and the precipitated white solid was filtered off. The filtrate was concentrated, and the residue was subjected to silica gel column chromatography (ethyl acetate:hexane=0:100 to 30:70, volume ratio) to give the title compound (2.4 g, yield 57%) as an orange oil. MS 672 (MH+).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe precipitated white solid was filtered off
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d2e18b7c6f984c28a0feffc05293c6e5
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673942B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes