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

HRID 638815Notes

Reaction equation

HRID 638815 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.[F:33][C:34]1[N:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=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:4]=[CH:3][C:2]([C:37]6[CH:38]=[N:39][C:34]([F:33])=[CH:35][CH:36]=6)=[CH:7][CH:6]=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])[CH2:29][CH2:30]1

Participants

3

Reactant 2

HCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 68576237(11beta,16alpha,17beta)-11-(4-Bromophenyl)-17-cyclopropylcarbonyl-16-methylestra-4,9-dien-3-one

Product 1

HCID 44451378(11beta,16alpha,17beta)-17-Cyclopropylcarbonyl-11-[4-(6-fluoropyridin-3-yl)phenyl]-16-methylestra-4,9-dien-3-oneYield 65%

Procedure

(11β,16α,17β)-11-(4-Bromophenyl)-17-cyclopropylcarbonyl-16-methylestra-4,9-dien-3-one and 6-fluoro-3-pyridinylboronic acid were used as described in example 1 step h. Purification by LCMS followed by lyophilisation gave the product (65% yield). 1H NMR (400 MHz, CDCl3): δ 0.34 (s, 3H), 0.80-2.85 (m, 24H), 4.45 (d, J=7 Hz, 1H), 5.80 (s, 1H), 7.00 (dd, J=8 and 3 Hz, 1H), 7.25-7.29 (m, 2H), 7.44-7.48 (m, 2H), 7.95 (dt, J=8 and 3 Hz, 1H), 8.41 (d, J=3 Hz, 1H).

Workup

  1. customPurification by LCMS

Sources & evidence

ORD record
ord-ae5d53ea62b24b7fadf5601cfe300113
Source dataset
uspto-grants-2010_04
Patent number
US07691836B2

Reaction notes

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