Sodium Carbonate → HCID 58335627, compound

HRID 1890698Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6](B(O)O)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].Br[C:18]1[N:23]=[C:22]([C:24]2[N:28]3[N:29]=[C:30]([N:33]4[CH2:37][CH2:36][CH2:35][C@@H:34]4[C:38]4[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[CH:39]=4)[CH:31]=[CH:32][C:27]3=[N:26][CH:25]=2)[CH:21]=[CH:20][CH:19]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:1][C:2]1[CH:7]=[C:6]([C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([C:24]3[N:28]4[N:29]=[C:30]([N:33]5[CH2:37][CH2:36][CH2:35][C@@H:34]5[C:38]5[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[CH:39]=5)[CH:31]=[CH:32][C:27]4=[N:26][CH:25]=3)[N:23]=2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

In step 16-3, 2-fluoropyridin-4-ylboronic acid (97%) (9.6 g, 66 mmol), Pd(dppf)Cl2 (1.3 g, 1.65 mmol) and 2N Na2CO3 (50 mL, 99 mmol) were added to a suspension of (R)-3-(6-bromopyridin-2-yl)-6-(2-(3-fluorophenyl)pyrrolidin-1-yl)imidazo[1,2-b]pyridazine (16-2) (14.5 g, 33 mmol) in 1,4-dioane (250 mL). The mixture was degassed for 15 minute using N2 and then heated at 110° C. for 3 hours. The mixture was filtered through a celite pad and rinsed with ethyl acetate (EtOAc). The filtrate was washed with brine, dried over Na2SO4, and concentrated to give (R)-3-(2′-fluoro-2,4′-bipyridin-6-yl)-6-(2-(3-fluorophenyl)pyrrolidin-1-yl)imidazo[1,2-b]pyridazine (16-3) as a dark oil, which was used in the next step without further purification. LC/MS: 455.2 (M+H+).

Workup

customThe mixture was degassed for 15 minute
filtrationThe mixture was filtered through a celite pad
washrinsed with ethyl acetate (EtOAc)
washThe filtrate was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-e0fa568a1c8741549783490a99ffcecd
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507488B2

Reaction notes

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