Dimethylformamide → HCID 58993595, compound

HRID 391448Notes

Reaction equation

HRID 391448 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:16][O:17][CH2:18][C:19]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)[CH:7]=1.[CH3:38][N:39](C)C=O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C-]#N.[Zn+2].[C-]#N>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:7]=[C:2]([C:38]#[N:39])[CH:3]=[C:4]([CH2:16][O:17][CH2:18][C:19]3([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:23][CH2:24]3)[CH:5]=2)=[CH:9][CH:10]=1)#[N:15]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 58993705HCID 58993705, compound

Product 1

HCID 58993595HCID 58993595, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

tert-Butyl 4-(((5-bromo-4′-cyanobiphenyl-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (52 mg, 0.09 mmol), tetrakis(triphenylphosphine) palladium(0) (14 mg, 0.01 mmol), and zinc cyanide (12 mg, 0.1 mmol) were combined in dimethylformamide (1.5 mL). The reaction mixture was degassed repeatedly using the freeze-pump-thaw method. After warming to room temperature, the reaction was heated at 90° C. for 1 h, cooled to room temperature, and concentrated. Flash chromatography on silica gel (30% ethyl acetate/hexanes) gave 15 mg (33%). 1H-NMR (CDCl3, 300 MHz) δ 7.78-7.75 (m, 3H), 7.52-7.55 (m, 2H), 7.31-7.33 (m, 4H), 7.20-7.23 (m, 2H), 4.41 (s, 2H), 3.70-3.77 (m, 2H), 3.43 (s, 2H), 2.97-3.06 (m, 2H), 2.17-2.21 (m, 2H), 1.78-1.88 (m, 2H), 1.40 (s, 9H). Mass spec.: 508.28 (MH)+.

Workup

  1. customThe reaction mixture was degassed repeatedly
  2. temperaturethe reaction was heated at 90° C. for 1 h
  3. temperaturecooled to room temperature
  4. concentrationconcentrated
  5. customFlash chromatography on silica gel (30% ethyl acetate/hexanes) gave 15 mg (33%)

Sources & evidence

ORD record
ord-f5f1b35c7335471b9791cb2ca7e2806c
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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