1-Methoxy-2-propanol → HCID 58237042, compound

HRID 1188935Notes

Reaction equation

HRID 1188935 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.[CH3:27][O:28][CH2:29][CH:30](O)[CH3:31].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH3:27][O:28][CH2:29][CH:30]([CH3:31])[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

Participants

6

Reactant 4

HCID 79001-Methoxy-2-propanol2×HCID 13831Tributylphosphine2×HCID 730421,1'-(Azodicarbonyl)dipiperidine2×HCID 66726144Ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate

Product 1

HCID 58237042HCID 58237042, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (2.0 g) in tetrahydrofuran (80 mL) were added 1-methoxypropan-2-ol (1.04 mL), tributylphosphine (2.46 mL) and 1,1′-(azodicarbonyl)dipiperidine (2.69 g) at room temperature. The mixture was stirred at 50° C. for 1 h. Then 1-methoxypropan-2-ol (0.5 mL), tributylphosphine (1.2 mL) and 1,1′-(azodicarbonyl)dipiperidine (1.34 g) were added to the mixture and the mixture was stirred at 50° C. overnight. The mixture was concentrated in vacuo. Ethyl acetate was added to the residue and insoluble materials were filtered off. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:9 to 6:4, volume ratio) to give the title compound (2.08 g, 87%) as a brown oil. MS 448 (MH+).

Workup

  1. stirringthe mixture was stirred at 50° C. overnight
  2. concentrationThe mixture was concentrated in vacuo
  3. additionEthyl acetate was added to the residue and insoluble materials
  4. filtrationwere filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=1:9 to 6:4, volume ratio)

Sources & evidence

ORD record
ord-d8b1be35004d4ead92da515341b53abb
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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