Tributylphosphine → {4-[3-Bromo-5-(3-morpholin-4-yl-propoxy)-phenylsulfanyl]-2-chloro-phenoxy}-acetic Acid Ethyl Ester

HRID 549545

Reaction equation

HRID 549545 reaction equation
[CH2:1]([O:3][C:4](=[O:6])[CH3:5])[CH3:2].[Br:7][C:8]1[CH:9]=[C:10]([S:15][C:16]2[CH:26]=[CH:25][C:19]([O:20]CC(O)=O)=[C:18]([Cl:27])[CH:17]=2)[CH:11]=[C:12]([OH:14])[CH:13]=1.O[CH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:6])[CH2:5][O:20][C:19]1[CH:25]=[CH:26][C:16]([S:15][C:10]2[CH:11]=[C:12]([O:14][CH2:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[CH:13]=[C:8]([Br:7])[CH:9]=2)=[CH:17][C:18]=1[Cl:27])[CH3:2]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 1995763-Morpholino-1-propanolHCID 67024266[4-(3-Bromo-5-hydroxy-phenylsulfanyl)-2-chloro-phenoxy]-acetic Acid Ethyl Acetate

Product 1

HCID 57791920{4-[3-Bromo-5-(3-morpholin-4-yl-propoxy)-phenylsulfanyl]-2-chloro-phenoxy}-acetic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

[4-(3-Bromo-5-hydroxy-phenylsulfanyl)-2-chloro-phenoxy]-acetic acid ethyl acetate (1.7 g; 4.07 mmol), N-(3-hydroxypropyl)morpholine (0.59 g; 4.07 mmol) and tributylphosphine (1.8 g; 7.33 mmol) were dissolved in THF (100 mL) in a dried reaction flask under an atmosphere of nitrogen. 1,1′-(Azodicarbonyl)dipiperidine (1.85 g; 7.33 mmol) dissolved in THF (50 mL) was added to the reaction mixture, which was stirred at room temperature for 16 h. The reaction mixture was evaporated to dryness and purified by flash chromatography (ethyl acetate:heptane). Yield: 1.1 g. HPLC-MS: m/z: 544.0 (M+); Rt: 1.78 min.

Workup

  1. additionwas added to the reaction mixture, which
  2. customThe reaction mixture was evaporated to dryness
  3. custompurified by flash chromatography (ethyl acetate:heptane)

Sources & evidence

ORD record
ord-ae040c11c28b47dcb2c53d3addc235f1
Source dataset
uspto-grants-2011_05
Patent number
US07943669B2

Linked notes

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