Triphenylphosphine → HCID 57748742, compound

HRID 1670643Notes

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

Participants

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

customDegas three times
temperatureCool the reaction mixture to room temperature
filtrationfilter through a plug of diatomaceous earth
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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