Dimethylformamide → 3-Morpholinoquinoxaline-6-carbaldehyde

HRID 929346노트

반응식

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

참가 물질

반응물 3

HCID 6228Dimethylformamide

HCID 12052Triethylsilane

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

생성물 1

HCID 866771723-Morpholinoquinoxaline-6-carbaldehyde수율 82.3%

반응 조건

온도: 90 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록: ord-d3f9f73119b04233ba77312fd2f6788f
출처 데이터셋: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09295671B2

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