Triphenylphosphine → 4-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2,6-difluorobenzonitrile

HRID 872547Notes

Reaction equation

HRID 872547 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]2[NH:14][N:13]=[CH:12][CH:11]=2)[CH:7]=[C:6]([F:15])[C:3]=1[C:4]#[N:5].O[CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[NH2:19][CH2:18][CH2:17][N:13]1[CH:12]=[CH:11][C:10]([C:8]2[CH:7]=[C:6]([F:15])[C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=2)=[N:14]1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 5363146Diisopropyl azodicarboxylateHCID 671718102,6-difluoro-4-(1H-pyrazol-5-yl)benzonitrile

Product 1

HCID 671716754-(1-(2-aminoethyl)-1H-pyrazol-3-yl)-2,6-difluorobenzonitrileYield 19.8%

Procedure

The title compound was prepared from 2,6-difluoro-4-(1H-pyrazol-5-yl)-benzonitrile (1.50 g, 7.31 mmol) and tert-butyl N-(2-hydroxyethyl)carbamate (0.96 ml, 6.09 mmol), triphenylphosphine (1.918 g, 7.31 mmol) and DIAD (1.200 ml, 6.09 mmol) using the method of Example 34 (c) affording 0.30 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.60 (m, 2H), 2.94 (t, 2H), 4.14 (t, 2H), 7.01 (d, 1H), 7.79 (m, 2H), 7.88 (d, 1H).

Sources & evidence

ORD record
ord-3c7a558832b14471a127ecb7b400050c
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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