Cyclopropylboronic acid → 1-(4-(methylsulfonyl)phenyl)-4-(1-(5-phenylpyridin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one

HRID 1518442Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([O:14][C:15]3[CH:20]=[CH:19][N:18]([C:21]4[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=4)[C:17](=[O:31])[CH:16]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.BrC1C=NC(N2CCC(OC3C=CN([C:52]4[CH:57]=[CH:56][C:55](S(C)(=O)=O)=[CH:54][CH:53]=4)C(=O)C=3)CC2)=NC=1.C1(B(O)O)CC1>C1COCC1>[CH3:30][S:27]([C:24]1[CH:25]=[CH:26][C:21]([N:18]2[CH:19]=[CH:20][C:15]([O:14][CH:11]3[CH2:12][CH2:13][N:8]([C:5]4[CH:4]=[CH:3][C:2]([C:52]5[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=5)=[CH:7][N:6]=4)[CH2:9][CH2:10]3)=[CH:16][C:17]2=[O:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28]

Participants

Conditions

Temperature: 120 °C

Procedure

Example 116 was prepared according to procedures described in Example 105 substituting 4-(1-(5-bromopyridin-2-yl)piperidin-4-yloxy)-1-(4-(methylsulfonyl)phenyl)pyridin-2(1H)-one for 4-(1-(5-bromopyrimidin-2-yl)piperidin-4-yloxy)-1-(4-(methylsulfonyl)phenyl)pyridin-2(1H)-one, substituting phenylboronic acid (Aldrich) for cyclopropylboronic acid and substituting DMF for THF. The reaction was heated under microwave conditions at 120° C. for 10 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.37 (d, J=2.45 Hz, 1 H), 7.95 (d, J=8.31 Hz, 2 H), 7.77 (dd, J=9.05, 2.20 Hz, 1 H), 7.51-7.63 (m, 5 H), 7.34 (t, J=7.58 Hz, 2 H), 7.21 (t, J=7.82 Hz, 1 H), 6.90 (d, J=8.80 Hz, 1H), 5.98-6.04 (m, 2 H), 4.65-4.73 (m, 1 H), 3.92-4.00 (m, 2 H), 3.26-3.34 (m, 2 H), 3.20 (s, 3 H), 1.92-2.00 (m, 2 H), 1.51-1.61 (m, 2 H). MS (ESI) 502 (M+H).

Workup

customExample 116 was prepared

Sources & evidence

ORD record: ord-d101bdf23d3c4a05946bcce16c684432
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232404B2

Reaction notes

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