Cesium fluoride → HCID 68209729, compound

HRID 1406317Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:27]2[N:31]=[CH:30][CH:29]=[N:28]2)=[C:6]([C@H:8]([O:10][C:11]2[C:12]([NH2:26])=[N:13][CH:14]=[C:15](B3OC(C)(C)C(C)(C)O3)[CH:16]=2)[CH3:9])[CH:7]=1.Br[C:33]1[CH:34]=[CH:35][C:36]2[CH:40]([OH:41])[CH2:39][S:38](=[O:43])(=[O:42])[C:37]=2[CH:44]=1.[F-].[Cs+]>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].CO>[NH2:26][C:12]1[N:13]=[CH:14][C:15]([C:33]2[CH:34]=[CH:35][C:36]3[CH:40]([OH:41])[CH2:39][S:38](=[O:42])(=[O:43])[C:37]=3[CH:44]=2)=[CH:16][C:11]=1[O:10][C@@H:8]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N:27]1[N:28]=[CH:29][CH:30]=[N:31]1)[CH3:9]

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture (R)-3-(1-(5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl)ethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine of preparation 109 (100 mg, 0.235 mmol), 6-bromo-2,3-dihydrobenzo[b]thiophen-3-ol-1,1 dioxide (92.6 mg, 1.5 eq), and CsF (126 mg, 3.5 eq) was added MeOH (2 mL). The mixture was thoroughly degassed and Pd(dppf)Cl2 (9.8 mg, 0.05 eq) was added. The mixture was heated in the microwave at 120° C. for 1 hr. LCMS showed the desired product mass. Mixture was filtered and purified with reverse phase preparative HPLC to give the title compound (66.08 mg, 58.4%).

Workup

customThe mixture was thoroughly degassed

Sources & evidence

ORD record: ord-8b4921952db34a3db4b8e4efdf8071a9
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916593B2

Reaction notes

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