Water → HCID 137329420, compound

HRID 1161059Notes

Reaction equation

HRID 1161059 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([CH3:24])([CH3:23])[O:17][SiH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:12][CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1.O.[CH3:26][N:27](C)C=O>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:19]([SiH2:18][O:17][C:16]([CH3:24])([CH3:23])[C:13]1[CH:14]=[CH:15][C:10]([C:8]([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([CH:3]=2)[C:26]#[N:27])=[O:9])=[CH:11][CH:12]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 137329421HCID 137329421, compound

Product 1

HCID 137329420HCID 137329420, compoundYield 63%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

Add tetrakis(triphenylphosphine)palladium (284 mg, 0.246 mmol) to a solution of (5-bromo-pyridin-3-yl)-[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-methanone (1.0 g, 2.46 mmol) and zinc cyanide (578 mg, 4.92 mmol) in dimethylformamide (25 mL) and stir. Purge solution with nitrogen and heat to 80° C. After 18 hours, add water (100 mL) and extract with ethyl acetate. Combine organic layers, dry over sodium sulfate, filter and concentrate under reduced pressure to give a residue. Purify the residue with flash chromatography eluting with 12.5% ethyl acetate:hexanes to yield the title compound as a white solid (550 mg, 63%): 1H NMR (DMSO-d6) δ 0.11 (s, 6H), 0.93 (s, 9H), 4.84 (bs, 2H), 7.53 (d, 2H), 7.83 (d, 2H), 8.61 (t, 1H), 9.09 (d, 1H), 9.26 (d, 1H).

Workup

  1. extractionextract with ethyl acetate
  2. dry with materialCombine organic layers, dry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. customto give a residue
  6. customPurify the residue with flash chromatography
  7. washeluting with 12.5% ethyl acetate

Sources & evidence

ORD record
ord-f78c3eaf8f98403e956ae01cca7c4b7c
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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