Triphenylphosphine → ethyl 3-(3-(6-aminonaphthalen-1-yloxy)propyl)-7-bromo-1H-indole-2-carboxylate

HRID 576283Notes

Reaction equation

HRID 576283 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.[NH2:30]C1C=C2C(=CC=1)C(O)=CC=C2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[NH2:30][C:26]1[CH:25]=[C:24]2[C:29](=[CH:28][CH:27]=1)[C:20]([O:19][CH2:18][CH2:17][CH2:16][C:7]1[C:6]3[C:10](=[C:2]([Br:1])[CH:3]=[CH:4][CH:5]=3)[NH:9][C:8]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:21][CH:22]=[CH:23]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 902956-AminonaphtholHCID 97268Di-tert-butyl azodicarboxylateHCID 68938945ethyl 7-bromo-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate

Product 1

HCID 68938609ethyl 3-(3-(6-aminonaphthalen-1-yloxy)propyl)-7-bromo-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 7-bromo-3-(3-hydroxypropyl)-1H-indole-2-carboxylate (EXAMPLE 1C) (100 mg), 6-aminonaphthalen-1-ol (98 mg) and triphenylphosphine, polymer supported (204 mg 0.613 mmol) in tetrahydrofuran (4 ml) was added di-tert-butyl diazene-1,2-dicarboxylate (141 mg). The reaction mixture was stirred at room temperature for 3 hours. The insoluble material was filtered off and the filtrate was concentrated. The residue was purified by flash chromatography (ethyl acetate in hexanes) to provide the title compound.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography (ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4afda756fbe6438c9affaf9bc70cc788
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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