Dimethylformamide → HCID 68467546, compound

HRID 1514235Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][C:6]=2[CH:19]=1.[CH3:20][N:21](C=O)C>CCOC(C)=O.O.[C-]#N.[Zn+2].[C-]#N>[C:20]([C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][C:6]=2[CH:19]=1)#[N:21]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1,1-dimethylethyl 7-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Preparation 73) (2.67 g, 8.14 mmol), zinc cyanide (1.715 g, 16.27 mmol) and tetakis(triphenylphosphine)palladium(0) (1.410 g, 1.220 mmol) in DMF (30 ml) was heated at 80° C. overnight. Additional tetakis(triphenylphosphine)palladium(0) (700 mg) was added and the yellow suspension heated at 80° C. for a further 5 hrs. The cooled reaction mixture was diluted with EtOAc/water, separated, and organics dried over anhydrous magnesium sulphate and evaporated. The crude was purified by flash chromatography eluting with EtOAc/iso-hexane 1:9. The combined fractions were evaporated to give the title compound (2.01 g) as a yellow solid. 6H (CDCl3, 400 MHz): 1.42 (9H, br.s), 3.81 (2H, t), 4.09 (2H, m), 4.43 (1H, s), 4.51 (1H, s), 7.09 (1H, m), 7.47-7.59 (2H, m).

Workup

temperaturethe yellow suspension heated at 80° C. for a further 5 hrs
customThe cooled reaction mixture
customseparated
dry with materialorganics dried over anhydrous magnesium sulphate
customevaporated
customThe crude was purified by flash chromatography
washeluting with EtOAc/iso-hexane 1:9
customThe combined fractions were evaporated

Sources & evidence

ORD record: ord-5d2eaf15bc7b4ef59c620a6624046624
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222245B2

Reaction notes

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