3-Fluoro-4-hydroxybenzonitrile → HCID 57964977, compound

HRID 1931654Notes

Reaction equation

HRID 1931654 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22](Cl)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[OH:33])[C:28]#[N:29]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:33][C:32]4[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][C:25]=4[F:24])=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27829443-Fluoro-4-hydroxybenzonitrileHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Product 1

HCID 57964977HCID 57964977, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[4-(4-Cyano-2-fluoro-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester was prepared according to General Procedure B by the reaction of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19) with 3-fluoro-4-hydroxybenzonitrile (available from Alfa Aesar, Ward Hill, Mass., USA) in dimethylformamide. 1H NMR (400 MHz, DMSO-d6) δ 1.43 (s, 9H), 1.98-2.07 (m, 4H), 2.99-3.07 (m, 2H), 4.07-4.12 (m, 2H), 5.00-5.05 (m, 1H), 7.76-7.80 (m, 1H), 7.88-7.90 (m, 1H), 8.16-8.19 (m, 1H), 8.50 (s, 1H), 8.57 (s, 1H). Mass spectrum MH+=439.

Sources & evidence

ORD record
ord-62f35880bbe24e82964a706407029291
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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