Triphenylphosphine → Diethyl 1-{3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropyl}-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

HRID 1521703Notes

Reaction equation

HRID 1521703 reaction equation
O[CH2:2][C:3]([CH3:14])([CH3:13])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[NH:15]1[C:19]2=[N:20][C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:23]=[C:18]2[CH:17]=[C:16]1[C:29]([O:31][CH2:32][CH3:33])=[O:30].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:8]([O:7][C:6]([NH:5][CH2:4][C:3]([CH3:14])([CH3:13])[CH2:2][N:15]1[C:19]2=[N:20][C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:23]=[C:18]2[CH:17]=[C:16]1[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:12])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 21263232tert-butyl N-(3-hydroxy-2,2-dimethylpropyl)carbamateHCID 67236396Diethyl 1H-pyrrolo[2,3-B]pyridine-2,6-dicarboxylate2×

Product 1

HCID 67238212Diethyl 1-{3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropyl}-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (3-hydroxy-2,2-dimethylpropyl)carbamate (2.13 g, 10.5 mmol), diethyl 1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (Intermediate D, 2.50 g, 9.53 mmol), and triphenylphosphine (5.00 g, 19.1 mmol) in THF (15 mL) is added diisopropyl azodicarboxylate (3.95 mL, 19.1 mmol). The reaction is stirred at room temperature for 64 h. The solvent is removed in vacuo and the crude material is purified via silica gel chromatography using a gradient elution of 0-30% ethyl acetate/hexanes to afford the title compound as a yellow oil which crystallized upon standing (4.20 g, 99%). LCMS: 478.86 (M+Na+).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe crude material is purified via silica gel chromatography
  3. washa gradient elution of 0-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-14ae0bcfb645472e936ec00d7aa7470c
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

Loading…