Dimethylformamide → HCID 57970871, compound

HRID 1044363Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][CH2:15][N:14]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=4)[CH2:13]3)[C:9]2=[O:28])=[C:4]([CH3:29])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:36][N:37](C)C=O>[C-]#N.[Zn+2].[C-]#N.[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>[CH3:29][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][CH2:15][N:14]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=3)[CH2:13]2)[C:9]1=[O:28])[C:36]#[N:37]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(4-bromo-2-methylphenyl)-7-[5-(trifluoromethyl)pyridin-2-yl]-2,7-diazaspiro[4.5]decan-1-one (63.6 mg, 0.000136 mol), zinc cyanide (32 mg, 0.00027 mol), potassium carbonate (0.056 g, 0.00041 mol) and tetrakis(triphenylphosphine) palladium(0) (8 mg, 0.000007 mol) in N,N-dimethylformamide (0.5 mL, 0.006 mol) was stirred at 100° C. for 2 days. The reaction mixture was cooled to ambient temperature and purified by prep-HPLC (under pH ˜10) to afford the desired product. LC-MS: 415.2 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
custompurified by prep-HPLC (under pH ˜10)

Sources & evidence

ORD record: ord-721269721fb648bcb3915f6cf79a0ed0
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563570B2

Reaction notes

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