Cesium carbonate → HCID 118116299, compound

HRID 1774626Notes

Reaction equation

HRID 1774626 reaction equation
Br[C:2]1[C:7](=[O:8])[N:6]([CH3:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([N:16]3[CH2:27][CH2:26][N:25]4[C:18](=[CH:19][C:20]5[CH2:21][C:22]([CH3:29])([CH3:28])[CH2:23][C:24]=54)[C:17]3=[O:30])[C:11]=2[CH2:31][OH:32])[CH:3]=1.[NH2:33][C:34]1[CH:39]=[CH:38][N:37]=[C:36]([N:40]2[CH2:44][CH2:43][CH:42]([C:45]([OH:47])=[O:46])[CH2:41]2)[N:35]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C=O)C>[CH3:28][C:22]1([CH3:29])[CH2:21][C:20]2[CH:19]=[C:18]3[N:25]([CH2:26][CH2:27][N:16]([C:12]4[C:11]([CH2:31][OH:32])=[C:10]([C:4]5[CH:3]=[C:2]([NH:33][C:34]6[CH:39]=[CH:38][N:37]=[C:36]([N:40]7[CH2:44][CH2:43][CH:42]([C:45]([OH:47])=[O:46])[CH2:41]7)[N:35]=6)[C:7](=[O:8])[N:6]([CH3:9])[CH:5]=5)[CH:15]=[CH:14][N:13]=4)[C:17]3=[O:30])[C:24]=2[CH2:23]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)2×HCID 118116776HCID 118116776, compoundHCID 118116851HCID 118116851, compound

Product 1

HCID 118116299HCID 118116299, compoundYield 13.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A 100 mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 10-[4-(5-bromo-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-(hydroxymethyl)pyridin-2-yl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-9-one 102b (497 mg, 1.0 mmol), 102a (312 mg, 1.5 mmol), Pd2(dba)3 (92 mg, 0.10 mmol), XantPhos (4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene, CAS Reg. No. 161265-03-8, 116 mg, 0.20 mmol), Cs2CO3 (652 mg, 2.0 mmol), and DMF (20 mL). After three cycles of vacuum/argon flush, the mixture was heated at 80° C. for 4 h. After this time the reaction was cooled to room temperature. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by reverse-phase prep-HPLC to afford 102c (82 mg, 13%) as a white solid. MS: [M+H]+ 625.4

Workup

  1. customA 100 mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customAfter three cycles of vacuum/argon flush
  3. temperatureAfter this time the reaction was cooled to room temperature
  4. filtrationIt was then filtered
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-2ab036de670848cebe59c953db6fe99e
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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