(Pyridin-4-yl)boronic acid → (11beta,16alpha,17beta)-17-Cyclopropylcarbonyl-16-methyl-11-[4-(4-pyridinyl)phenyl]estra-4,9-dien-3-one

HRID 638821Notes

Reaction equation

HRID 638821 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.[N:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=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:36]6[CH:37]=[CH:38][N:33]=[CH:34][CH:35]=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 2734379(Pyridin-4-yl)boronic acidHCID 68576237(11beta,16alpha,17beta)-11-(4-Bromophenyl)-17-cyclopropylcarbonyl-16-methylestra-4,9-dien-3-one

Product 1

HCID 44451341(11beta,16alpha,17beta)-17-Cyclopropylcarbonyl-16-methyl-11-[4-(4-pyridinyl)phenyl]estra-4,9-dien-3-oneYield 44%

Procedure

(11β,16α,17β)-11-(4-Bromophenyl)-17-cyclopropylcarbonyl-16-methylestra-4,9-dien-3-one and 4-pyridinylboronic acid were applied as described in example 1 step h. Purification by HPLC followed by crystallisation (acetonitrile/water) gave the product (44% yield). 1H NMR (400 MHz, CDCl3): δ 0.33 (s, 3H), 0.84-2.85 (m, 24H), 4.46 (d, J=7 Hz, 1H), 5.81 (s, 1H), 7.26-7.30 (m, 2H), 7.48-7.50 (m, 2H), 7.55-7.59 (m, 2H), 8.63-8.65 (m, 2H).

Workup

  1. customPurification by HPLC
  2. customfollowed by crystallisation (acetonitrile/water)

Sources & evidence

ORD record
ord-33c4aaf3ac8740c9a436cf57c5402dc9
Source dataset
uspto-grants-2010_04
Patent number
US07691836B2

Reaction notes

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