Cesium carbonate → HCID 22730744, compound

HRID 2356100Notes

Reaction equation

HRID 2356100 reaction equation
O1CCCOB1[C:7]1[CH:37]=[CH:36][C:10]([C:11]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][CH2:24][CH2:25][S:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:19]([N+:33]([O-:35])=[O:34])[CH:18]=2)(=[O:16])=[O:15])=[O:12])=[CH:9][CH:8]=1.[F:38][C:39]([F:56])([F:55])[C:40]1[C:49](Cl)=[CH:48][C:47]2[C:42](=[C:43]([C:51]([F:54])([F:53])[F:52])[CH:44]=[CH:45][CH:46]=2)[N:41]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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]>[F:55][C:39]([F:38])([F:56])[C:40]1[CH:49]=[C:48]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][CH2:24][CH2:25][S:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[C:19]([N+:33]([O-:35])=[O:34])[CH:18]=3)(=[O:15])=[O:16])=[O:12])=[CH:36][CH:37]=2)[C:47]2[C:42](=[C:43]([C:51]([F:52])([F:53])[F:54])[CH:44]=[CH:45][CH:46]=2)[N:41]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 22730365HCID 22730365, compoundHCID 22730739HCID 22730739, compound

Product 1

HCID 22730744HCID 22730744, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of Example 214D (100 mg, 0.15 mmol) and 2,8-bistrifluoromethyl-3-chloroquinoline (100 mg, 0.343 mmol) in dioxane (2 mL) was treated with Pd2(dba)3 (10 mg, 0.011 mmol), P(t-Bu)3 (20 mg, 0.1 mmol) and Cs2CO3 (150 mg, 0.50 mmol), purged with argon, sealed, and heated to 85° C. for 18 hours. The mixture was concentrated and the concentrate was dissolved in 1:1 DMSO/methanol (1 mL) and filtered. The filtrate was purified by preparative HPLC (using a Nova-Pak HR C-18 column and a solvent system varying in gradient from 10-95% acetonitrile/water containing 0.1% TFA) to provide the desired product. MS (ESI(+)) m/e 721 (M+H)+, m/e 719 (M−H)−; 1H NMR (500 MHz, DMSO-d6) δ 8.80 (t, 1H), 8.67 (d, 1H), 8.41 (d, 1H), 8.14 (d, 1H), 8.12 (d, 2H), 8.08 (s, 1H), 7.97 (dd, 1H), 7.91 (t, 1H), 7.77 (d, 2H), 7.38 (dt, 2H), 7.28 (td, 2H), 7.24 (d, 1H), 7.17 (tt, 1H), 3.69 (q, 2H), 3.31 (t, 2H).

Workup

  1. custompurged with argon
  2. customsealed
  3. concentrationThe mixture was concentrated
  4. dissolutionthe concentrate was dissolved in 1:1 DMSO/methanol (1 mL)
  5. filtrationfiltered
  6. customThe filtrate was purified by preparative HPLC (

Sources & evidence

ORD record
ord-6aea3a652efa4c83a56a79218ead7f14
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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