1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 59310141, compound

HRID 1513042Notes

Reaction equation

HRID 1513042 reaction equation
C(O[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[N:13][C:14]=1I)=[O:7])(C)(C)C.[Cl:20][C:21]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH2:31][C:32]2[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[C:34]([F:40])[C:33]=2[F:41])=[CH:24][C:22]=1[NH2:23].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>O1CCCC1.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].C(O)(=O)C>[Cl:20][C:21]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH2:31][C:32]2[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[C:34]([F:40])[C:33]=2[F:41])=[CH:24][C:22]=1[N:23]1[C:14]2=[N:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=[C:9]2[NH:8][C:6]1=[O:7]

Participants

8

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 593096392-Chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyanilineHCID 59309789HCID 59309789, compound

Product 1

HCID 59310141HCID 59310141, compoundYield 43.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 5-(tert-butoxycarbonylamino)-6-iodopyridine-2-carboxylate (0.14 g), 2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyaniline (0.18 g), tris-(dibenzylideneacetone)dipalladium(0) (10 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (13 mg) and sodium tert-butoxide (48 mg) in tetrahydrofuran (3 mL) was heated at reflux for 22 hours. The reaction mixture was cooled to room temperature. To the reaction mixture was added acetic acid (0.02 mL), and the mixture was directly purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/2−1/3) to give the title compound (81 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 22 hours
  3. customthe mixture was directly purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/2−1/3)

Sources & evidence

ORD record
ord-d0b134ac89e54ebcae3701bbbd01bea8
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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