4-Fluorobenzylic alcohol → HCID 86725590, compound

HRID 878625Notes

Reaction equation

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

Participants

Reactant 2

HCID 680224-Fluorobenzylic alcohol

HCID 178455196HCID 178455196, compound

Product 1

HCID 86725590HCID 86725590, compoundYield 43%

Procedure

The title compound was prepared in 43% yield from 2-[4-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-5-hydroxypyrazol-1-yl]pyridine-4-carbonitrile and (4-fluorophenyl)methanol according to the procedure for the preparation of Example 39, part C. 1H NMR (400 MHz, CDCl3): δ 0.00 (6H, s), 0.85 (9H, s), 2.50 (2H, t, J=6.4 Hz), 3.68 (2H, d, J=6.4 Hz), 5.12 (2H, s), 6.98-7.02 (2H, m), 7.30-7.34 (3H, m), 7.54 (1H, s), 7.98 (1H, s), 8.58 (1H, d, J=5.2 Hz). [M+H] Calc'd for C24H29FN4O2Si, 453; Found, 453.

Sources & evidence

ORD record: ord-0f3a2a00156e4093ac835572da808fc6
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987461B2

Reaction notes

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