Benzyl Alcohol → HCID 18435807, compound

HRID 2304760Notes

Reaction equation

HRID 2304760 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]2[OH:16].[CH2:17](O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(Cl)Cl.C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]2[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 54677169Ethyl 5-bromo-3-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 18435807HCID 18435807, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution containing 2.04 g of ethyl 5-bromo-3-hydroxyindole-2-carboxylate, 3.94 g of benzyl alcohol and 3.34 g of di-tert-butyl azodicarboxylate in 30 mL of THF and 15 mL of CH2Cl2 at −78° C. was treated dropwise with a solution containing 3.81 g of triphenylphosphine in 15 mL of CH2Cl2. The resulting reaction mixture was warmed slowly to 0° C. upon consumption of the starting material (monitored by TLC). 800 μL of acetic acid was added and after 30 min the solvents were removed under vacuum and the excess of acetic acid was removed by coevaporation with toluene. The crude product was filtered over a pad of silica gel eluting with CH2Cl2. The organic phase was concentrated to dryness and the solid was swished with hexane to give 2.13 g of the title compound as a white solid.

Workup

  1. additionwas treated dropwise with a solution
  2. customThe resulting reaction mixture
  3. customwere removed under vacuum
  4. customthe excess of acetic acid was removed by coevaporation with toluene
  5. filtrationThe crude product was filtered over a pad of silica gel eluting with CH2Cl2
  6. concentrationThe organic phase was concentrated to dryness

Sources & evidence

ORD record
ord-addfc6939e0744cf8a32b1fda5ca49bb
Source dataset
uspto-grants-2002_08
Patent number
US06436965B1

Reaction notes

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