Triphenylphosphine → 3-(4-Fluorobenzyl)-7-(tetrahydro-2H-pyran-2-yloxy)-7,8,9,10-tetrahydropyrrolo[3',2':4,5]pyrido[2,3-c]azepin-6(3H)-one

HRID 640711Notes

Reaction equation

HRID 640711 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:20]([NH:22][O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)=[O:21])[C:15]([CH2:16][CH2:17][CH2:18]O)=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]4[C:15]([CH2:16][CH2:17][CH2:18][N:22]([O:23][CH:24]5[CH2:29][CH2:28][CH2:27][CH2:26][O:25]5)[C:20]4=[O:21])=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 866021111-(4-fluorobenzyl)-4-(3-hydroxypropyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

Product 1

HCID 686651933-(4-Fluorobenzyl)-7-(tetrahydro-2H-pyran-2-yloxy)-7,8,9,10-tetrahydropyrrolo[3',2':4,5]pyrido[2,3-c]azepin-6(3H)-oneYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-fluorobenzyl)-4-(3-hydroxypropyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxamide (149 mg, 0.35 mmol) in THF (4 mL), was added PPh3 (110 mg, 0.42 mmol) and DIAD (85 mg, 0.42 mmol). The resulting mixture was stirred for 1 h at room temperature. The mixture was concentrated. Purification by flash chromatography (Biotage) over silica gel (100% ethyl acetate) afforded the title product as brown oil (18.5 mg, 13% yield). LC-MS (APCl, M+H+): 410.1. HPLC: 96% purity.

Workup

  1. concentrationThe mixture was concentrated
  2. customPurification by flash chromatography (Biotage) over silica gel (100% ethyl acetate)

Sources & evidence

ORD record
ord-fcca3cc413a84ba59dc318d37dfcbfa2
Source dataset
uspto-grants-2010_04
Patent number
US07692014B2

Reaction notes

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