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Triphenylphosphine → HCID 57748742, compound

HRID 1670643
Notes
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Reaction equation

HRID 1670643 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@@H:9]2[CH2:17][N:16]3[C@H:11]([CH2:12][O:13][CH2:14][CH2:15]3)[CH2:10]2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.[F:21][C:22]1[CH:23]=[CH:24][C:25]2=[C:26]([CH:47]=1)[O:27][CH2:28][C:29]1[C:45]([F:46])=[CH:44][CH:43]=[CH:42][C:30]=1/[C:31]/2=[CH:32]\B1OC(C)(C)C(C)(C)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[O-].[Na+]>O1CCCC1.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:21][C:22]1[CH:23]=[CH:24][C:25]2=[C:26]([CH:47]=1)[O:27][CH2:28][C:29]1[C:45]([F:46])=[CH:44][CH:43]=[CH:42][C:30]=1/[C:31]/2=[CH:32]\[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@@H:9]2[CH2:17][N:16]3[C@H:11]([CH2:12][O:13][CH2:14][CH2:15]3)[CH2:10]2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 10942334Sodium MethoxideHCID 57748785HCID 57748785, compoundHCID 67335785HCID 67335785, compound

Product 1

HCID 57748742HCID 57748742, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Degas three times a mixture of (4-bromo-2-nitro-phenyl)-((7S,8aS)-hexahydro-pyrrolo[2,1-c][1,4]oxazin-7-yl)-amine (0.011 mol, 4.0 g), (E)-3,7-difluoro-11-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-ylmethylene)-6,11-dihydro-dibenzo[b,e]oxepine (0.012 mol, 4.76 g), triphenylphosphine (0.0031 mol, 0.8 g) and sodium methoxide (0.03 mol, 1.6 g) in tetrahydrofuran/methanol (3:1) (120 mL) with nitrogen. Add palladium (II) acetate (1.0 mmol, 240 mg) to the reaction mixture and degas again three times with nitrogen. Heat the reaction mixture at 70° C. for 4 h. Cool the reaction mixture to room temperature, filter through a plug of diatomaceous earth and concentrate the filtrate under reduced pressure to obtain the title compound (5.0 g, crude).

Workup

  1. customDegas three times
  2. temperatureCool the reaction mixture to room temperature
  3. filtrationfilter through a plug of diatomaceous earth
  4. concentrationconcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-d24a4b987e6d4ffcad5b8557338b2fd0
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07994164B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes