Nitrogen → HCID 86696291, compound

HRID 2175158Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([F:30])[C:5]2[N:6]([C:8]([S:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][C:16]([N:22]3[CH2:26][CH2:25][C@H:24]([N:27]([CH3:29])[CH3:28])[CH2:23]3)=[CH:15]4)=[N:9][N:10]=2)[CH:7]=1.N#N.C([Sn](CCCC)(CCCC)[C:38]([O:40][CH2:41][CH3:42])=[CH2:39])CCC>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:41]([O:40][C:38]([C:2]1[CH:3]=[C:4]([F:30])[C:5]2[N:6]([C:8]([S:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][C:16]([N:22]3[CH2:26][CH2:25][C@H:24]([N:27]([CH3:28])[CH3:29])[CH2:23]3)=[CH:15]4)=[N:9][N:10]=2)[CH:7]=1)=[CH2:39])[CH3:42]

Participants

Conditions

Temperature: 90 °C

Procedure

The solution of (85.1) (175 mg, 0.359 mmol) and PdCl2(PPh3)2 (37.8 mg, 0.054 mmol) in DMF (10 ml) was bubbled by N2 for 5 min. tributyl(1-ethoxyvinyl)stannane (195 mg, 0.539 mmol) was added. The reaction tube was flushed by N2 for 5 min again and sealed. The sealed-tube was stirred at 90° C. for 2 h. Then the reaction was continued at 110° C. for 16 h. The mixture was evaporated to dryness and the residue was purified by column chromatography (CombiFlash, ISCO, eluent MeOH/DCM from 0 to 10%) to afford the target product (40 mg, 30% pure, yield 6.98%). LCMS (method A): [M+H]+=479.1, tR=1.92 min.

Workup

additionwas added
customThe reaction tube was flushed by N2 for 5 min again
customsealed
waitThen the reaction was continued at 110° C. for 16 h
customThe mixture was evaporated to dryness
customthe residue was purified by column chromatography (CombiFlash, ISCO, eluent MeOH/DCM from 0 to 10%)
customto afford the target product (40 mg, 30% pure, yield 6.98%)

Sources & evidence

ORD record: ord-09b58d5dc59f4df3b8d7f0d4fa79952d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062045B2

Reaction notes

Loading…