Cesium carbonate → n-Pyridin-3-yl-n-{1-[4'-(pyrrolidin-1-ylsulfonyl)biphenyl-2-yl]ethyl}pyridin-3-amine

HRID 563952Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:10]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH3:9].CC1(C)C(C)(C)OB([C:31]2[CH:36]=[CH:35][C:34]([S:37]([N:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)(=[O:39])=[O:38])=[CH:33][CH:32]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+]>[Pd].C1COCC1>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N:10]([CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[C:31]2[CH:36]=[CH:35][C:34]([S:37]([N:40]3[CH2:41][CH2:42][CH2:43][CH2:44]3)(=[O:39])=[O:38])=[CH:33][CH:32]=2)[CH3:9])[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=1

Participants

Conditions

Temperature: 160 °C

Procedure

In 0.5-2 mL microwave vial with stirbar was placed crude product N-(1-(2-bromophenyl)ethyl)-N-(pyridin-3-yl)pyridin-3-amine (3-2) (0.030 g, 0.08 mmol), 1-[4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonyl]pyrrolidine (0.040 g, 0.12 mmol), Pd (dppf) Cl2 dichloromethane adduct (0.013 g, 0.0 16 mmol), Cs2CO3 (1 M aq. solution, 0.5 mL, 0.5 mmol) and THF (0.5 mL). The vial was sealed and heated in microwave to 160° C. for 10 min. The organic phase was filtered through packed celite, concentrated and dried. Reverse phase chromatography yielded a TFA salt Analytical LCMS: single peak (214 nm), 2.426 min. 1H NMR (300 MH, CDCl3): δ 9.00 (s, 1 H), 8.65 (s, 1 H), 8.35 (d, J=5.1 Hz, 1 H), 8.17-8.25 (m, 2 H), 7.75-7.82 (m, 4 H), 7.56-7.7.67 (m, 4 H), 7.45-7.47 (m, 2 H), 7.28-7.31 (m, 1 H), 6.20 (q, J=6-6 Hz, 1 H), 3.19-3.24 (m, 4 H), 2.07 (d, J=6.6 Hz, 3 H), 1.76-1.80 (m, 4 H). m/e (m+1): 485.1.

Workup

customThe vial was sealed
filtrationThe organic phase was filtered
concentrationconcentrated
customdried

Sources & evidence

ORD record: ord-66b827a87e8e4ca09980f4831922cb55
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067607B2

Reaction notes

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