Dimethylformamide → 3-Morpholinoquinoxaline-6-carbaldehyde

HRID 929346Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:9]2)=[CH:4][CH:3]=1.[SiH](CC)(CC)CC.CN([CH:28]=[O:29])C>>[O:15]1[CH2:16][CH2:17][N:12]([C:8]2[CH:7]=[N:6][C:5]3[C:10]([N:9]=2)=[CH:11][C:2]([CH:28]=[O:29])=[CH:3][CH:4]=3)[CH2:13][CH2:14]1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 12052Triethylsilane

HCID 533635264-(7-Bromoquinoxalin-2-yl)morpholine

Product 1

HCID 866771723-Morpholinoquinoxaline-6-carbaldehydeYield 82.3%

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-(7-bromoquinoxalin-2-yl)morpholine (59 g, 0.2 mol, 1.0 eq.) in DMF (500 mL) was added TEA (139 mL, 1.0 mol, 5.0 eq.), Et3SiH (127 mL, 0.8 mol, 4.0 eq) and Pd(dppf)Cl2CH2Cl2 (8.16 g, 0.01 mol, 0.05 eq.). The resulting mixture was stirred at 90° C. for 12 h in an autoclave under CO (1 MPa), then cooled and concentrated. The resulting residue was purified by flash column chromatography (EA/PE=1/1) to afford 3-morpholinoquinoxaline-6-carbaldehyde as a yellow solid (40 g, 82.3%).

Workup

temperaturecooled
concentrationconcentrated
customThe resulting residue was purified by flash column chromatography (EA/PE=1/1)

Sources & evidence

ORD record: ord-d3f9f73119b04233ba77312fd2f6788f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09295671B2

Reaction notes

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