Potassium Carbonate → 10-[4-(1H-benzimidazol-2-yloxy)phenyl]-6,7,8,9-tetrahydropyrido[2,3-b]indolizine

HRID 573285Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:24]=[CH:23][C:12]([O:13][C:14]3[NH:18][C:17]4[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=4[N:15]=3)=[CH:11][CH:10]=2)O1.Br[C:27]1[C:28]2[N:39]=[CH:38][CH:37]=[CH:36][C:29]=2[N:30]2[C:35]=1[CH2:34][CH2:33][CH2:32][CH2:31]2.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:18]1[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[N:15]=[C:14]1[O:13][C:12]1[CH:11]=[CH:10][C:9]([C:27]2[C:28]3[N:39]=[CH:38][CH:37]=[CH:36][C:29]=3[N:30]3[C:35]=2[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1H-benzo[d]imidazole (320 mg), 10-bromo-6,7,8,9-tetrahydropyrido[2,3-b]indolizine (217 mg) and K2CO3 (119 mg) in DME (4 mL) and water (1 mL) was added Pd(PPh3)4 (100 mg). The mixture was heated at 150° C. for 40 min under microwave irradiation. The mixture was poured into water and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (43.4 mg).

Workup

extractionextracted with AcOEt
customThe organic layer was separated
washwashed with brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record: ord-14eb3b254427486893c5845be4f840de
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029536B2

Reaction notes

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