Dimethylformamide → HCID 58993529, compound

HRID 391375Notes

Reaction equation

HRID 391375 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([CH2:21][O:22][CH2:23][C:24]3[CH:25]=[C:26]([C:34]4[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=4)[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=3)[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:42][N:43](C)C=O>[C-]#N.[Zn+2].[C-]#N>[C:40]([C:37]1[CH:38]=[CH:39][C:34]([C:26]2[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=[C:24]([CH2:23][O:22][CH2:21][C:8]3([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([C:42]#[N:43])[CH:3]=4)[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)[CH:25]=2)=[CH:35][CH:36]=1)#[N:41]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 58993677HCID 58993677, compound

Product 1

HCID 58993529HCID 58993529, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
120 °C

Procedure

A mixture of tert-Butyl 4-(3-bromophenyl)-4-(((4′-cyano-5-(trifluoromethyl)biphenyl-3-yl)methoxy)methyl)piperidine-1-carboxylate (150 mg, 0.238 mmol), zinc cyanide (33.6 mg, 0.286 mmol), palladium tetrakis triphenylphosphine (27.5 mg, 0.024 mmol), and dimethylformamide (1 mL) was charged to a conical vial and purged with nitrogen for 5 minutes. The vial was sealed and heated at 120° C. for 2 hours and then held at room temperature overnight. The resulting mixture was filtered through a syringe tip filter and applied directly to a silica gel column. Gradient elution with 5-40% ethyl acetate/hexanes afforded the product as a clear oil (83 mg, 61%). 1H-NMR (CDCl3, 500 MHz) δ ppm 7.76 (m, 2H), 7.68 (s, 1H), 7.56-7.64 (m, 4H), 7.45-7.49 (m, 1H), 7.38-7.43 (m, 2H), 7.34 (s, 1H), 3.69 (m, 2H), 3.45 (s, 2H), 3.05 (m, 2H), 2.10 (m, 2H), 1.88 (m, 2H), 1.42 (s, 9H). Mass spec.: 576.17 (MH)+.

Workup

  1. additionwas charged to a conical vial and
  2. custompurged with nitrogen for 5 minutes
  3. customThe vial was sealed
  4. filtrationThe resulting mixture was filtered through a syringe tip
  5. filtrationfilter
  6. washGradient elution with 5-40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6d6037bc9da74dbf977cd22ba13de0bf
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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