Triphenylphosphine → Diethyl 1H-indole-2,6-dicarboxylate

HRID 1748282Notes

Reaction equation

HRID 1748282 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=2)[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].O[CH2:21][CH:22]([CH3:32])[CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:27]([O:26][C:25]([NH:24][CH2:23][CH:22]([CH3:32])[CH2:21][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=2)[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:31])([CH3:30])([CH3:29])[CH3:28].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=2)[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11424042Tert-butyl (3-hydroxy-2-methylpropyl)carbamateHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2×

Product 2

HCID 44754779Diethyl 1H-indole-2,6-dicarboxylateYield 331%HCID 67235256HCID 67235256, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl 1H-indole-2,6-dicarboxylate (Intermediate A, 1.9 g, 7.4 mmol), tert-butyl (3-hydroxy-2-methylpropyl)carbamate (2.8 g, 14.8 mmol) and triphenylphosphine (4.9 g, 18.5 mmol) in THF (35 mL) at 0° C. is added diisopropyl azodicarboxylate (3.8 mL, 18.5 mmol). The mixture is stirred for 16 h at room temperature and then the solvent is removed. The residue is filtered through a pad of silica (300 g, 240-400 mesh) using 30% EtOAc in heptane to afford of mixture of the title compound and diethyl 1H-indole-2,6-dicarboxylate (3.2 g) which is used in the next step without further purification.

Workup

  1. customthe solvent is removed
  2. filtrationThe residue is filtered through a pad of silica (300 g, 240-400 mesh)

Sources & evidence

ORD record
ord-9d06d379dbc148269a7e693e34233fb9
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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