(6-Methoxypyridin-3-yl)boronic acid → (11beta,16alpha,17beta)-17-Cyclopropylcarbonyl-11-[4-(6-methoxypyridin-3-yl)phenyl]-16-methylestra 4,9-dien-3-one

HRID 638814Notes

Reaction equation

HRID 638814 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:25][C@@:23]3([CH3:24])[C@@H:19]([CH2:20][C@@H:21]([CH3:31])[C@@H:22]3[C:26]([CH:28]3[CH2:30][CH2:29]3)=[O:27])[C@H:18]3[C:9]2=[C:10]2[C:15]([CH2:16][CH2:17]3)=[CH:14][C:13](=[O:32])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[CH3:33][O:34][C:35]1[N:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1>>[CH:28]1([C:26]([C@H:22]2[C@H:21]([CH3:31])[CH2:20][C@H:19]3[C@H:18]4[C:9]([C@@H:8]([C:5]5[CH:6]=[CH:7][C:2]([C:38]6[CH:39]=[N:40][C:35]([O:34][CH3:33])=[CH:36][CH:37]=6)=[CH:3][CH:4]=5)[CH2:25][C@:23]23[CH3:24])=[C:10]2[C:15](=[CH:14][C:13](=[O:32])[CH2:12][CH2:11]2)[CH2:16][CH2:17]4)=[O:27])[CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 68576237(11beta,16alpha,17beta)-11-(4-Bromophenyl)-17-cyclopropylcarbonyl-16-methylestra-4,9-dien-3-one

Product 1

HCID 44451394(11beta,16alpha,17beta)-17-Cyclopropylcarbonyl-11-[4-(6-methoxypyridin-3-yl)phenyl]-16-methylestra 4,9-dien-3-oneYield 54%

Procedure

Reaction of (11β,16α,17β)-11-(4-bromophenyl)-17-cyclopropylcarbonyl-16-methylestra-4,9-dien-3-one and 6-methoxy-3-pyridinylboronic acid using the procedure described in example 1 step h afforded the title compound (54% yield). 1H NMR (400 MHz, CDCl3): δ 0.35 (s, 3H), 0.84-0.99 (m, 6H), 1.08-1.15 (m, 1H), 1.33-1.39 (m, 1H), 1.45-1.54 (m, 1H), 1.62-1.70 (m, 2H), 1.91-1.97 (m, 1H), 2.01-2.08 (m, 1H), 2.24-2.53 (m, 6H), 2.58-2.64 (m, 2H), 2.68-2.85 (m, 3H), 3.98 (s, 3H), 4.44 (d, J=8 Hz, 1H), 5.80 (s, 1H), 6.80 (d, J=8 Hz, 1H), 7.23 (d, J=7 Hz, 2H), 7.44 (d, J=7 Hz, 2H), 7.75-7.79 (m, 1H), 8.36-8.38 (m, 1H).

Sources & evidence

ORD record
ord-7a9191b5ea404156a80e62a2a4cb0ae7
Source dataset
uspto-grants-2010_04
Patent number
US07691836B2

Reaction notes

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