Dimethylformamide → HCID 68110257, compound

HRID 627734Notes

Reaction equation

HRID 627734 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH:9]([F:11])[F:10])=[CH:4][N:3]=1.[CH3:12][N:13](C=O)C>[C-]#N.[C-]#N.[Zn+2].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>[F:10][CH:9]([F:11])[C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([C:12]#[N:13])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 75176245HCID 75176245, compound

Product 1

HCID 68110257HCID 68110257, compound

Reagents, catalysts & solvents 2

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

Procedure

A solution of 2-chloro-5-difluoromethyl-3-methyl-pyridine (337 mg, 1.898 mmol), Zn(CN)2 (159 mg, 1.328 mmol) and Pd(PPh3)4 (132 mg, 0.114 mmol) in DMF (10 ml) was stirred for 10 min at 120° C. in a microwave, filtered over hyflo and washed with water and brine. The combined aqueous layers were extracted with TBME, the combined organic layers were dried over sodium sulfate, filtered and concentrated. 5-Difluoromethyl-3-methyl-pyridine-2-carbonitrile was obtained as a yellow oil after flash chromatography on silica gel (cyclohexane/EtOAc gradient 0-3 min 100:0, 3-35 min 100:0 to 80:20). ESI MS: 169 [M+H]; 1H NMR (400 MHz, CDCl3): δ=8.68 (s, 1H), 7.84 (s, 1H), 6.75 (t, 1H), 2.65 (s, 3H).

Workup

  1. filtrationfiltered over hyflo
  2. washwashed with water and brine
  3. extractionThe combined aqueous layers were extracted with TBME
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e16f11a0107d4a20b29ef53fe5761fe8
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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