Dimethylformamide → HCID 68970352, compound

HRID 1726130Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:23]2[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=2)[O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30][N:31](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:23]2[CH:28]=[CH:27][C:26]([C:30]#[N:31])=[CH:25][CH:24]=2)[O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 4-[(4-bromo-phenyl)-(6-methyl-pyridin-2-yloxy)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (2.00 g, 4.33 mmol) and zinc cyanide (305 mg, 2.60 mmol) in DMF (20 mL) under nitrogen was added DPPF (48 mg, 0.087 mmol) and Pd2(dba)3 (40 mg, 0.043 mmol). The resulting suspension was warmed to 130° C. and stirred for 5 hours. Standard work-up and purification gave 4-[(4-cyano-phenyl)-(6-methyl-pyridin-2-yloxy)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (1.4 g, 79%) as a yellow solid.

Workup

customStandard work-up and purification

Sources & evidence

ORD record: ord-83dc3f929d8c4fb49f47b23f7eabd85b
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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