Dimethylformamide → HCID 67520980, compound

HRID 1926278Notes

Reaction equation

HRID 1926278 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[N:21][C:22]([NH2:36])=[C:23]([C:25]4[N:26]=[CH:27][C:28]5[C:33]([CH:34]=4)=[CH:32][C:31](Br)=[CH:30][CH:29]=5)[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:37][N:38](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[N:21][C:22]([NH2:36])=[C:23]([C:25]4[N:26]=[CH:27][C:28]5[C:33]([CH:34]=4)=[CH:32][C:31]([C:37]#[N:38])=[CH:30][CH:29]=5)[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 67520734HCID 67520734, compound

Product 1

HCID 67520980HCID 67520980, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

Following the General Procedure for Conversion of Bromo(het)aryl to Cyano(het)aryl, 4-{4-[6-amino-5-(6-bromoisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (220 mg, 0.240 mmol) was reacted with Pd(PPh3)4 (38.9 mg, 0.0336 mmol) and zinc cyanide (28.2 mg, 0.240 mmol) in DMF (6 ml). The crude product was purified by chromatography on silica gel (8 g) eluting with DCM (100 ml), 1% (100 ml), 2% (100 ml), 3% (100 ml) and 4% (50 ml) MeOH/DCM to give the title compound as a yellow solid. MS(ES+): m/z=496.22 (100) [MH+]. HPLC: tR=2.82 min (ZQ3, polar—5 min).

Workup

  1. customThe crude product was purified by chromatography on silica gel (8 g)
  2. washeluting with DCM (100 ml), 1% (100 ml), 2% (100 ml), 3% (100 ml) and 4% (50 ml) MeOH/DCM

Sources & evidence

ORD record
ord-24d5e12a85884bad8e30bea07d0503fc
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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