Methanol → (E)-4-(2-(2-(Quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-8-yl)morpholine

HRID 718662Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14]([CH:16]=O)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.[CH3:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1.C[Si](Br)(C)C.CO>CN(C=O)C>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1/[CH:18]=[CH:16]/[C:14]1[N:15]=[C:8]2[C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:12][CH:11]=[N:10][N:9]2[CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of compound 5e (10 g, 43 mmol) and 2-methylquinoline (4.6 g, 32 mmol) in DMF (10 mL) was added TMSBr (2.9 g, 19 mmol) dropwise. The reaction mixture was stirred at 80° C. for 2 h. MeOH (10 mL) was added. The solids formed were collected by filtration and washed with Et2O (2×50 mL) to obtain compound 57c as a yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C21H19N5O: 358.2 (M+H). Found: 358.3.

Workup

customThe solids formed
filtrationwere collected by filtration
washwashed with Et2O (2×50 mL)

Sources & evidence

ORD record: ord-20a174ab630244f0a5b32e76b9f2bde3
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193736B2

Reaction notes

Loading…