Dimethylformamide → HCID 24759309, compound

HRID 1672390Notes

Reaction equation

[CH:1]1([N:7]2[CH2:27][CH2:26][C:9]3([N:13]([CH2:14][C:15]4[CH:20]=[CH:19][C:18](B(O)O)=[C:17]([F:24])[CH:16]=4)[CH2:12][C@H:11]([OH:25])[CH2:10]3)[C:8]2=[O:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:30]1[CH:31]=[CH:32][C:33]([C:36]([NH:38][CH:39]([CH3:41])[CH3:40])=[O:37])=[N:34][CH:35]=1.CN(C=O)C.C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:1]1([N:7]2[CH2:27][CH2:26][C:9]3([N:13]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([C:30]5[CH:31]=[CH:32][C:33]([C:36]([NH:38][CH:39]([CH3:41])[CH3:40])=[O:37])=[N:34][CH:35]=5)=[C:17]([F:24])[CH:16]=4)[CH2:12][C@H:11]([OH:25])[CH2:10]3)[C:8]2=[O:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of (4-{[(3R)-7-cyclohexyl-3-hydroxy-6-oxo-1,7-diazaspiro[4.4]non-1-yl]-methyl}-2-fluorophenyl)boronic acid (24.0 mg, 0.0000614 mol; which was prepared by using procedures that were analogous to those described for the synthesis of Example 32, steps 1-3 using peak 2 from step 2) and 5-bromo-N-isopropylpyridine-2-carboxamide (18 mg, 0.000074 mol) in DMF (0.8 mL, 0.01 mol) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (1:1) (3.01 mg, 3.68E-6 mol) and potassium carbonate (25 mg, 0.00018 mol). The resulting mixture was heated at 130° C. under an atmosphere of nitrogen for 16 h to afford the desired product which was purified by prep-HPLC. LC/MS: 509.2 (M+1H)+.

Workup

customwhich was prepared

Sources & evidence

ORD record: ord-c5ec82f2f0e94fb88539cfbec2b3ff8a
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998959B2

Reaction notes

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