Triphenylphosphine → HCID 68423474, compound

HRID 1437706Notes

Reaction equation

[CH:1]1([N:4]2[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[C:11]([O:15][C:16]([N:18]1[C:22]2=[N:23][CH:24]=[C:25](O)[CH:26]=[C:21]2[CH:20]=[C:19]1[C:28]([N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[O:29])=[O:17])([CH3:14])([CH3:13])[CH3:12].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>O1CCCC1>[C:11]([O:15][C:16]([N:18]1[C:22]2=[N:23][CH:24]=[C:25]([O:10][CH:7]3[CH2:8][CH2:9][N:4]([CH:1]4[CH2:3][CH2:2]4)[CH2:5][CH2:6]3)[CH:26]=[C:21]2[CH:20]=[C:19]1[C:28]([N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[O:29])=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

To the solution of 73 mg (0.5 mmol) N-cyclopropyl-4-piperidinol in 2 ml tetrahydrofuran, 0.15 g (0.43 mmol) 5-hydroxy-2-(morpholine-4-carbonyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester and 0.14 g (0.52 mmol) triphenylphosphine were added and the suspension cooled to 0° C. Then, 0.12 g (0.52 mmol) diisopropyl azodicarboxylate was added and the resulting solution stirred for 20 hours at room temperature. The solvent was evaporated and the residue flash-chromatographed on silica gel with ethyl acetate:methanol (9:1 v/v) as eluant to give 0.16 g (81%) the product as a colorless gum.

Workup

customThe solvent was evaporated
customthe residue flash-chromatographed on silica gel with ethyl acetate:methanol (9:1 v/v) as eluant

Sources & evidence

ORD record: ord-ffc87d01fe0d4c3d8a8d40686e1e8817
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622466B2

Reaction notes

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