Benzophenone imine → HCID 86660407, compound

HRID 403225Notes

Reaction equation

HRID 403225 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[NH:10][C:11]2[CH2:12][O:13][CH2:14][C:15]([F:28])([F:27])[C@:16]([C:19]3[CH:24]=[C:23](Br)[CH:22]=[CH:21][C:20]=3[F:26])([CH3:18])[N:17]=2)=[CH:5][CH:4]=1.[C:43](=[NH:56])([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>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.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[NH:10][C:11]2[CH2:12][O:13][CH2:14][C:15]([F:28])([F:27])[C@:16]([C:19]3[CH:24]=[C:23]([N:56]=[C:43]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[CH:22]=[CH:21][C:20]=3[F:26])([CH3:18])[N:17]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 136809Benzophenone imineHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 23676156Sodium t-butoxideHCID 67468385(R)-N-(bis(4-methoxyphenyl)(phenyl)methyl)-5-(5-bromo-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine

Product 1

HCID 86660407HCID 86660407, compound

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of (R)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-5-(5-bromo-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine (intermediate A8A) (1.2 mmol) in toluene (15 ml) was added subsequently at 22° C. and under a argon atmosphere benzophenone imine (2.4 mmol), sodium tert-butoxide (3.6 mmol) and 2-di-t-butylphosphino-2′,4′,6′-triisopropylbiphenyl (0.12 mmol). To the mixture was added tris(dibenzylideneacetone) dipalladium chloroform adduct (0.036 mmol), the tube was sealed and heated to 105° C. for 3 h. The mixture was cooled to 22° C., partitioned between saturated aqueous NaHCO3 and ethyl acetate, the organic layer was dried and evaporated to give the crude (R)—N-(bis(4-methoxyphenyl)(phenyl)methyl)-5-(5-(diphenylmethyleneamino)-2-fluorophenyl)-6,6-difluoro-5-methyl-2,5,6,7-tetrahydro-1,4-oxazepin-3-amine (A9A) as a yellow oil. MS (ISN): m/z=738.5 [M−H]−.

Workup

  1. customthe tube was sealed
  2. temperatureThe mixture was cooled to 22° C.
  3. custompartitioned between saturated aqueous NaHCO3 and ethyl acetate
  4. customthe organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-c6b3465d08b34ece8dd8ea41c8909371
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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