1,4-Bis(diphenylphosphino)butane → HCID 90067224, compound
Reaction equation
C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[BH4-].[Na+].C([N:36]1[C:44]2[C:39](=[N:40][C:41]([C:46]3[CH:51]=[CH:50][C:49]([N:52]4[CH:56]=[C:55]5[CH2:57][N:58]([CH2:60][C:61]([F:64])([F:63])[F:62])[CH2:59][C:54]5=[N:53]4)=[CH:48][CH:47]=3)=[C:42]([Cl:45])[CH:43]=2)[N:38]=[C:37]1[O:65][C@H:66]1[C@H:70]2[O:71][CH2:72][C@@H:73]([OH:74])[C@H:69]2[O:68][CH2:67]1)C=C>C(O)C.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:45][C:42]1[CH:43]=[C:44]2[NH:36][C:37]([O:65][C@H:66]3[C@H:70]4[O:71][CH2:72][C@@H:73]([OH:74])[C@H:69]4[O:68][CH2:67]3)=[N:38][C:39]2=[N:40][C:41]=1[C:46]1[CH:51]=[CH:50][C:49]([N:52]2[CH:56]=[C:55]3[CH2:57][N:58]([CH2:60][C:61]([F:62])([F:63])[F:64])[CH2:59][C:54]3=[N:53]2)=[CH:48][CH:47]=1Participants
7
Procedure
A 4 mL vial was charged with palladium(II) acetate (2.6 mg, 0.012 mmol), 1,4-bis(diphenylphosphino)butane (3.0 mg, 7.03 μmol), and ethanol (0.1 ml). This catalyst mixture was degassed (3×) and stirred under nitrogen for 15 min. Sodium borohydride (3.5 mg, 0.093 mmol) was added to a stirred solution of (3R,3aR,6R,6aR)-6-[1-allyl-6-chloro-5-[4-[5-(2,2,2-trifluoroethyl)-4,6-dihydropyrrolo[3,4-c]pyrazol-2-yl]phenyl]imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol (9.5 mg, 0.016 mmol) in ethanol (0.15 ml) and DCM (0.05 ml). The sodium borohydride mixture was degassed (3×) and placed under nitrogen. The catalyst mixture was transferred via syringe to the sodium borohydride reaction mixture.
Workup
- customThis catalyst mixture was degassed (3×)
- customThe sodium borohydride mixture was degassed (3×)
- customThe catalyst mixture was transferred via syringe to the sodium borohydride reaction mixture
Sources & evidence
- ORD record
- ord-dd53a50fc00b4b6baa359f5a048b51ad
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09290517B2
Reaction notes
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