1-Naphthol → HCID 68936013, compound

HRID 576274Notes

Reaction equation

HRID 576274 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O-:13])=[O:12])=[C:7]2[CH2:14][CH2:15][CH2:16][OH:17].[C:19]1(O)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.[C:30]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:31]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:30][CH3:31])=[O:12])=[C:7]2[CH2:14][CH2:15][CH2:16][O:17][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 70051-NaphtholHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 131730595HCID 131730595, compound

Product 1

HCID 68936013HCID 68936013, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of EXAMPLE 402C (1.03 g), naphthalen-1-ol (519 mg), and triphenylphosphine (905 mg) in tetrahydrofuran (15 ml) at −10° C. was added di-tert-butyl azodicarboxylate (794 mg) slowly. After one hour, the reaction was allowed to warm to room temperature. Stirring was continued for two hours at room temperature. The reaction mixture was concentrated. The concentrate was purified by column chromatography on silica gel with 0-4% ethyl acetate in hexanes.

Workup

  1. waitwas continued for two hours at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. customThe concentrate was purified by column chromatography on silica gel with 0-4% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1a1a5c25e0b242d2b316560720801d5c
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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