Cesium carbonate → HCID 5330831, compound

HRID 2215072Notes

Reaction equation

HRID 2215072 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:78][C:79]1[C:84]([C:85]([C:87]2[C:92]([F:93])=[CH:91][CH:90]=[CH:89][C:88]=2[F:94])=[O:86])=[CH:83][CH:82]=[C:81]([NH2:95])[N:80]=1>O1CCOCC1.C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[NH2:78][C:79]1[N:80]=[C:81]([NH:95][C:15]2[CH:16]=[CH:17][C:12]([S:9]([N:8]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)(=[O:11])=[O:10])=[CH:13][CH:14]=2)[CH:82]=[CH:83][C:84]=1[C:85](=[O:86])[C:87]1[C:88]([F:94])=[CH:89][CH:90]=[CH:91][C:92]=1[F:93]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 1339209HCID 1339209, compoundHCID 5330840HCID 5330840, compound

Product 1

HCID 5330831HCID 5330831, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

A N,N-Dibenzyl-4-iodobenzenesulfonamide Compound 2a (20.4 mg, 0.044 mmol), Pd2(dba)3 (1.0 mg), BINAP (1.8 mg) and cesium carbonate (13 mg, 0.04 mmol) were added to a solution of Compound 1 (10 mg, 0.04 mmol) in dioxane (0.20 mL) and toluene (0.25 mL). The resulting mixture was stirred in an oil-bath (at a temperature of from about 90 to about 100° C.) for about 24 hours. The mixture was cooled to rt then water (20 mL) was added and extracted with methylene chloride (4×20 mL). The organic layers were combined, dried and evaporated, then separated by chromatography (on silica gel, eluting with 1:1 ethyl acetate:hexane) to give a 4-[[6-amino-5-(2,6-difluorobenzoyl)-2-pyridinyl]amino]-N,N-bis(phenylmethyl)benzenesulfonamide Compound 2b (11 mg, 46% yield) as a yellow powder. 1H NMR (300 MHz, CDCl3) δ 9.0 (s, br, 2H), 7.80 (d, 2H), 7.62 (d, 2H), 7.40–7.58 (m, 2H), 7.35–6.95 (m, 12H), 6.40 (s, br, 1H), 6.12 (d, 1H), 7.35 (s, 4H); MS (ESI) m/z: 585 (M+H+), 607 (M+Na+).

Workup

  1. extractionextracted with methylene chloride (4×20 mL)
  2. customdried
  3. customevaporated
  4. customseparated by chromatography (on silica gel, eluting with 1:1 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-35a451513f18463b845165112392df69
Source dataset
uspto-grants-2006_09
Patent number
US07109220B2

Reaction notes

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